Substituted benzoyl derivatives as herbicides

ABSTRACT

What is described are derivatives of benzoyl derivatives of the formula (I) and their use as herbicides.  
                 
 
In this formula (I), R 1 , R 2  and R 3  are different radicals, X is a bridge atom selected from the group consisting of oxygen and sulfur and Het is a saturated heterocyclic group which comprises oxygen and carbon atoms.

The invention relates to the technical field of herbicides, inparticular that of the herbicides from the group of thebenzoylcyclohexanediones and benzoylpyrazoles for selectivelycontrolling broad-leaved weeds and weed grasses in crops of usefulplants, in particular in crops of rice.

From various publications, it is already known that certain benzoylderivatives have herbicidal properties. Thus, WO 99/10327 and WO99/10328 disclose benzoylcyclohexanediones and benzoylpyrazolonescarrying a heterocyclyl or heteroaryl radical, attached via a multiatombridge, in the 3-position of the phenyl ring.

However, the compounds known from these publications frequently haveinsufficient herbicidal activity.

It is an object of the present invention to provide further herbicidallyactive compounds which have improved herbicidal properties compared withthe compounds known from the prior art.

It has now been found that benzoyl derivatives which carry certainheterocyclyl radicals, attached via a two-atom bridge, in thethree-position of the phenyl ring are particularly suitable asherbicides. Accordingly, the present invention provides compounds of theformula (I) and salts thereof

in which the radicals and indices are as defined below:

-   R¹, R² independently of one another are hydrogen, mercapto, nitro,    halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-haloalkynyl,    C₃-C₆-cycloalkyl, —OR⁴, OCOR⁴, OSO₂R⁴, S(O)NR⁴, SO₂OR⁴, SO₂N(R⁴)₂,    NR⁴SO₂R⁴, NR⁴COR⁴, C₁-C₆-alkyl-S(O)_(n)R⁴, C₁-C₆-alkyl-OR⁴,    C₁-C₆-alkyl-OCOR⁴, C₁-C₆-alkyl-OSO₂R⁴, C₁-C₆-alkyl-SO₂OR⁴,    C₁-C₆-alkyl-SO₂N(R⁴)₂ or C₁-C₆-alkyl-NR⁴COR⁴;-   R³ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl;-   R⁴ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, phenyl or phenyl-C₁-C₆-alkyl, where the six    last-mentioned radicals are substituted by s radicals selected from    the group consisting of hydroxy, mercapto, amino, cyano, nitro,    thiocyanato, OR³, SR³, N(R³)₂, ═NOR³, OCOR³, SCOR³, NR³COR³, CO₂R³,    COSR³, CON(R³)₂, C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino,    C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl and    C₁-C₄-alkylsulfonyl;-   Het is a fully saturated heterocyclic group whose ring atoms consist    of carbon and oxygen atoms, where    -   the total number of ring atoms is p,    -   the number of oxygen atoms is r,    -   the number of carbon atoms is (p−r) and    -   Het may be substituted by n radicals R⁵;-   n is 0, 1 or 2;-   p is 5, 6 or 7;-   r is 1 or 2;-   s is , 1, 2 or 3;-   x is O or S(O)_(n);-   R⁵ is hydroxy, mercapto, amino, cyano, nitro, halogen, formyl,    C₁-C₆-alkylamino, C₁-C₈-dialkylamino, C₁-C₆-alkoxycarbonyl,    C₁-C₆-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy or R⁵ together with the carbon atom to which it is    attached forms a carbonyl group;-   Q is a radical of group Q1 or Q2;-   R⁶, R⁷ independently of one another are hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl or C₃-C₆-cyclopropyl;-   R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl,    C₁-C₆-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl,    phenyloxycarbonyl or phenylsulfonyl, where the phenyl ring of the    four last-mentioned radicals is substituted by s radicals selected    from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.

Depending on external conditions such as solvent and pH, the compoundsof the formula (I) according to the invention can exist in differenttautomeric structures. Depending on the nature of the substituents, thecompounds of the formula (I) contain an acidic proton, which can beremoved by reaction with a base. Examples of suitable bases arehydrides, hydroxides and carbonates of alkali metals and alkaline earthmetals such as lithium, sodium, potassium, magnesium and calcium, andalso ammonia and organic amines such as triethylamine and pyridine. Suchsalts are likewise provided by the invention.

In the formula (I) and in all subsequent formulae, alkyl radicals havingmore than two carbon atoms can be straight-chain or branched. Alkylradicals are, for example, methyl, ethyl, n- or isopropyl, n-, iso-, t-or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and1,3-dimethylbutyl, preferably methyl or ethyl.

If a group is substituted by a plurality of radicals, this is to beunderstood as meaning that this group is substituted by one or moreidentical or different of the radicals mentioned.

Cycloalkyl denotes a carbocyclic saturated ring system having three tonine carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl.Analogously, cycloalkenyl denotes a monocyclic alkenyl group havingthree to nine carbon ring members, for example cyclopropenyl,cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond maybe located in any position. In the case of composed radicals such ascycloalkylalkenyl, the radical mentioned first may be in any position ofthe radical mentioned second.

“Heterocyclic group” is to be understood as meaning radicals such as2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydropyranyl,3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-hexahydrooxepanyl,3-hexahydrooxepanyl, 4-hexahydrooxepanyl, 1,3-dioxolan-4-yl,1,3-dioxan-4-yl, 1,3-dioxan-5-yl and 1,4-dioxan-2-yl. Het is preferablyunsubstituted or substituted by 1, 2, 3 or 4 methyl groups and/or 1 or 2carbonyl groups.

In the case of a disubstituted amino group such as dialkylamino thesetwo substituents may be identical or different.

Halogen denotes fluorine, chlorine, bromine or iodine. Haloalkyl,-alkenyl and -alkynyl denote alkyl, alkenyl and alkynyl, respectively,which are partially or fully substituted by halogen, preferably byfluorine, chlorine and/or bromine, in particular by fluorine orchlorine, for example CF₃, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl, CCl₃, CHCl₂,CH₂CH₂Cl, CH═CHCl, CH═CCl₂, C≡CCH₂Cl; haloalkoxy is, for example, OCF₃,OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ or OCH₂CH₂Cl; this appliescorrespondingly to haloalkenyl and other halogen-substituted radicals.

If a group is polysubstituted, this is to be understood as meaning thatthe general principles of the construction of chemical compounds must betaken into consideration when combining the various substituents, i.e.that the formation of compounds which are known to the skilled worker asbeing chemically unstable or impossible must be avoided.

Depending on the nature and linkage of the substituents, the compoundsof the formula (I) can exist as stereoisomers. If, for example, one ormore asymmetric carbon atoms are present, enantiomers and diestereomersmay occur. Stereoisomers can be obtained by customary separationmethods, for example by chromatographic separation methods, from themixtures which are obtained in the preparation. It is also possible toprepare stereoisomers selectively by employing stereoselective reactionsusing optically active starting materials and/or auxiliaries. Theinvention relates to all stereoisormers and their mixtures which areembraced by formula (I), but not specifically defined.

Compounds of the formula (I) in which

-   R¹, R² independently of one another are hydrogen, nitro, halogen,    C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,    C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl, —OR⁴, S(O)NR⁴,    SO₂OR⁴, SO₂N(R⁴)₂, NR⁴SO₂R⁴ or C₁-C₆-alkyl-S(O)_(n)R⁴;-   R⁴ is hydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,    C₃-C₆-cycloalkyl, phenyl or phenyl-C₁-C₄-alkyl, where the six    last-mentioned radicals are substituted by s radicals selected from    the group consisting of cyano, nitro, R³, OR³, SR³ and N(R³)₂ and    the other substituents and indices are in each case as defined    above, have been found to be advantageous.

Preference is given to compounds of the formula (I), in which

-   R³ is hydrogen;-   R⁵ is cyano, nitro, halogen, C₁-C₄-alkoxycarbonyl,    C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, or R⁵ together with the carbon atom to which it is    attached forms a carbonyl group; R⁵ is, in particular, methyl or    methoxy, or R⁵ together with the carbon atom to which it is attached    forms a carbonyl group and the other substituents and indices are in    each case as defined above.

Particular preference is given to compounds of the formula (I), in which

-   R⁶, R⁷ independently of one another are hydrogen or C₁-C₄-alkyl, in    particular methyl or ethyl, or cyclopropyl;-   R⁸ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylsulfonyl,    C₁-C₄-haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl,    phenyloxycarbonyl or phenylsulfonyl, where the phenyl ring of the    four last-mentioned radicals is substituted by s radicals selected    from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, and the other    substituents and indices are in each case as defined above.

Very particular preference is given to compounds of the formula (I) inwhich

-   R¹ is chlorine, bromine, iodine, nitro, methyl, thiomethyl,    thioethyl, methylsulfonyl, ethylsulfonyl or methoxy;-   R² is bromine, chlorine, methylsulfonyl or ethylsulfonyl;-   R² is located in the 4-position of the phenyl rings;-   R⁸ is hydrogen;-   Het is 3-tetrahydrofuranyl, 3-tetrahydropyranyl,    4-tetrahydropyranyl, 1,3-dioxan-5-yl or γ-butyrolacton-2-yl,    and the other substituents and indices are in each case as defined    above.

In the formulae mentioned below, substituents and symbols have, unlessdefined otherwise, the same meaning as described under formula (I).

Compounds according to the invention in which Q is Q1 can be prepared,for example, according to the method shown in Scheme 1 by base-catalyzedreaction of a compound of the formula (IIIa), in which T is halogen,hydroxy or alkoxy with a cyclohexanedione (II) in the presence of acyanide source. Such methods are described, for example, in EP-A 0 369803 and EP-B 0 283 261.

Compounds according to the invention in which Q is Q2 and R8 is hydrogencan be prepared, for example, by the method shown in Scheme 2. To thisend, a compound of the formula (IIIa) is, either in the presence of adehydrating agent such as DCC or after conversion into its acidchloride, reacted under base catalysis with a pyrazole of the formula(IV) and finally treated with a cyanide source. These methods aredescribed, for example, in EP-A 0 369 803.

Compounds according to the invention of the formula (I) in which R⁸ is aradical different from hydrogen can be prepared, for example, accordingto Scheme 3 by substitution reactions known per se to the person skilledin the art. To this end, compounds of the formula (Ib) are reacted withcompounds of the formula (V) in which E is a nucleophilicallyexchangeable leaving group. Such methods are known, for example, from WO99/10328.

Compounds of the formula (IIIa), in which T is OH can be prepared, forexample, according to Scheme 4 from compounds of the formula (Ib), inwhich Hal is halogen and R¹⁰ is alkoxy or OH.

Compounds of the formula (IIIa) are also obtainable by reactionsaccording to Scheme 5.

Compounds of the formulae (VIa) and (VIb) are known from the literatureor can be prepared by known methods as described, for example, in WO96/26200 and in the German patent application No. 10144412.5, which wasunpublished at the priority date of the present invention.

The compounds of the formula (I) according to the invention have anoutstanding herbicidal activity against a broad spectrum of economicallyimportant monocotyledonous and dicotyledonous harmful plants. The activesubstances also effect good control of perennial weeds which produceshoots from rhizomes, root stocks or other perennial organs and whichare difficult to control. In this context, it is generally immaterialwhether the substances are applied before sowing, pre-emergence orpost-emergence. Specifically, some representatives of themonocotyledonous and dicotyledonous weed flora which can be controlledby the compounds according to the invention may be mentioned by way ofexample, without a restriction to certain species being intended to takeplace as a result of the mention. Amongst the monocotyledonous weedspecies, those on which the active substances act efficiently are, forexample, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria,Setaria and Cyperus species from the annual group and, among theperennial species, Agropyron, Cynodon, Imperata and Sorghum and alsoperennial Cyperus species. In the case of dicotyledonous weed species,the spectrum of action extends to species such as, for example, Galium,Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida,Matricaria and Abutilon among the annuals and Convolvulus, Cirsium,Rumex and Artemisia in the case of the perennial weeds. Harmful plantsoccurring under the specific cultivation conditions of rice such as, forexample, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus andCyperus, are also outstandingly well controlled by the active substancesaccording to the invention. If the compounds according to the inventionare applied to the soil surface before germination, then the weedseedlings are either prevented completely from emerging or the weedsgrow until they have reached the cotyledon stage, but then their growthstops and they finally die completely after three to four weeks haveelapsed. When the active substances are applied post-emergence to thegreen parts of the plants, growth also stops drastically a very shorttime after the treatment and the weed plants remain at the stage ofgrowth at the time of application, or they die completely after acertain time, so that in this manner competition by the weeds, which isharmful to the crop plants, is eliminated at a very early stage and in asustained manner. In particular, the compounds according to theinvention are highly active against Amaranthus retroflexus, Avena sp.,Echinochloa sp., Cyperus serotinus, Lolium multiforum, Setaria viridis,Sagittaria pygmaea, Scirpus juncoides, Sinapis sp. and Stellaria media.

Although the compounds according to the invention have excellentherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops such as wheat, barley, rye,rice, corn, sugar beet, cotton and soybeans, are damaged only to aninsignificant extent or not at all. In particular, they areoutstandingly well-tolerated in wheat, corn and rice. For these reasons,the present compounds are very highly suitable for selectivelycontrolling undesired vegetation in stands of agriculturally usefulplants or in stands of ornamental plants.

On account of their herbicidal properties, the active substances canalso be employed for controlling harmful plants in crops of knowngenetically modified plants or genetically modified plants yet to bedeveloped. As a rule, the transgenic plants are distinguished byparticularly advantageous properties, for example by resistances tocertain pesticides, especially certain herbicides, resistances to plantdiseases or plant pathogens, such as certain insects or microorganismssuch as fungi, bacteria or viruses. Other particular properties relate,for example, to the harvested material with respect to quantity,quality, storability, composition and specific constituents. Thus,transgenic plants with an increased starch content or in which thequality of the starch is altered, or those having a different fatty acidcomposition of the harvested material, are known.

The compounds of the formula (I) according to the invention or theirsalts are preferably used in economically important transgenic crops ofuseful plants and ornamentals, e.g. of cereals such as wheat, barley,rye, oats, sorghum and millet, rice, cassava and maize, or else crops ofsugar beet, cotton, soybeans, oil seed rape, potatoes, tomatoes, peasand other types of vegetable. The compounds of the formula (I) canpreferably be employed as herbicides in crops of useful plants which areresistant, or have been made resistant by recombinant methods, to thephytotoxic effect of herbicides.

Traditional ways of generating novel plants which have modifiedcharacteristics in comparison with existing plants consist, for example,in traditional breeding methods and the generation of mutants.Alternatively, novel plants with modified characteristics can begenerated using recombinant procedures (see, for example, EP-A-0221044,EP-A-0131624). For example, a number of cases have been described of

-   -   recombinant modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (for example WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to certain herbicides        of the glutosinate type (cf., for example, EP-A-0242236,        EP-A-242246) or of the glyphosate type (WO 92/00377) or of the        sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, with the capability        of producing Bacillus thuringiensis toxins (Bt toxins) which        make the plants resistant to certain pests (EP-A-0142924,        EP-A-0193259),    -   transgenic crop plants having a modified fatty acid composition        (WO 91/13972).

A large number of molecular-biological techniques with which noveltransgenic plants with modified properties can be generated are known inprinciple; see, for example, Sambrook et al., 1989, Molecular Cloning, ALaboratory Manual, 2nd Ed., Cold Spring Harbor Laboratory Press, ColdSpring Harbor, N.Y.; or Winnacker “Gene und Klone” [Genes and Clones],VCH Weinheim 2nd Edition 1996 or Christou, “Trends in Plant Science” 1(1996) 423-431).

To carry out such recombinant manipulations, nucleic acid moleculeswhich permit a mutagenesis or a sequence modification by recombinationof DNA sequences can be introduced into plasmids. For example, it ispossible with the aid of the abovementioned standard methods to carryout base exchanges, to remove subsequences or to add natural orsynthetic sequences. Adapters or linkers may be added in order to linkthe DNA fragments to each other.

For example, plant cells with a reduced activity of a gene product cansuccessfully be generated by expressing at least one suitable antisenseRNA, a sense RNA to achieve a cosuppression effect or by expressing atleast one suitably constructed ribozyme which specifically cleavestranscripts of the abovementioned gene product.

To this end, it is possible to use firstly DNA molecules which encompassall of the coding sequence of a gene product including any flankingsequences which may be present and secondly DNA molecules which onlyencompass parts of the coding sequence, it being necessary for theseparts to be of sufficient length to cause an antisense effect in thecells. Also possible is the use of DNA sequences which have a highdegree of homology with the coding sequences of a gene product which arenot entirely identical thereto.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any compartment of the plant cell.However, to achieve localization in a particular compartment, it ispossible for example to link the coding region with DNA sequences whichguarantee localization in a certain compartment. Sequences of this typeare known to the person skilled in the art, (see, for example, Braun etal., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci.USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be regenerated by known techniques togive intact plants. In principle, the transgenic plants can be plants ofany desired plant species, i.e. both monocotyledonous and dicotyledonousplants.

Transgenic plants are thus obtainable which have modified properties asa result of overexpression, suppression or inhibition of homologous(=natural) genes or gene sequences, or expression of heterologous(=foreign) genes or gene sequences.

When the active substances according to the invention are used intransgenic crops, effects which are specific for application in theparticular transgenic crop, for example a modified or specificallywidened spectrum of weeds which can be controlled, altered applicationrates which can be employed for application, preferably good combiningability with the herbicides, to which the transgenic crop is resistant,and an effect on growth and yield of the transgenic crop plants, oftenoccur in addition to the effects against harmful plants which can beobserved in other crops. Subject matter of the invention is thereforealso the use of the compounds according to the invention as herbicidesfor controlling harmful plants in transgenic crop plants.

The substances according to the invention additionally also haveoutstanding growth-regulatory properties in crop plants. They engage inthe plants' metabolism in a regulatory fashion and can thus be employedfor the targeted control of plant constituents and for facilitatingharvesting, such as, for example, triggering desiccation and stuntedgrowth. Moreover, they are also suitable for generally controlling andinhibiting undesired vegetative growth without destroying the plants inthe process. Inhibiting the vegetative growth plays an important role inmany monocotyledonous and dicotyledonous crops since lodging can bereduced, or prevented completely, hereby.

The compounds according to the invention can be employed in the form ofwettable powders, emulsifiable concentrates, sprayable solutions, dustsor granules in the customary preparations. Accordingly, the inventionalso provides herbicidal agents comprising compounds of the formula (I).The compounds of the formula (I) can be formulated in various ways,depending on the prevailing biological and/or chemico-physicalparameters. Examples of suitable formulations which are possible are:wettable powders (WP), water-soluble powders (SP), water-solubleconcentrates, emulsifiable concentrates (EC), emulsions (EW), such asoil-in-water and water-in-oil emulsions, sprayable solutions, suspensionconcentrates (SC), oil- or water-based dispersions, oil-misciblesolutions, capsule suspensions (CS), dusts (DP), seed-dressing products,granules for spreading and soil application, granules (GR) in the formof microgranules, spray granules, coated granules and adsorptiongranules, water-dispersible granules (WG), water-soluble granules (SG),ULV formulations, microcapsules and waxes. These individual formulationtypes are known in principle and are described, for example, inWinnacker-Küchler, “Chemische Technologie” [Chemical Engineering],Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986, Wade van Valkenburg,“Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “SprayDrying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflätchenaktive Äthylenoxidaddukte” [Surface-active ethylene oxideadducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie”, Volume 7, C. Hauser Verlag Munich, 4th Ed.1986.

Wettable powders are preparations which are uniformly dispersible inwater and which, in addition to the active substance, also contain ionicand/or nonionic surfactants (wetters, dispersants), for examplepolyoxyethylated alkylphenols, polyoxethylated fatty alcohols,polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates,alkanesulfonates, alkylbenzenesulfonates, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodium lignosulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate, inaddition to a diluent or inert substance. To prepare the wettablepowders, the herbicidal active substances are ground finely, for examplein customary equipment such as hammer mills, blowing mills and air-jetmills, and simultaneously or subsequently mixed with the formulationauxiliaries.

Emulsifiable concentrates are prepared by dissolving the activesubstance in an organic solvent, e.g. butanol, cyclohexanone,dimethylformamide, xylene or else higher-boiling aromatics orhydrocarbons or mixtures of the organic solvents with addition of one ormore ionic and/or nonionic surfactants (emulsifiers). Examples ofemulsifiers which can be used are: calcium alkylarylsulfonates such ascalcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fattyacid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide/ethylene oxide condensates, alkylpolyethers, sorbitan esters such as, for example, sorbitan fatty acidesters or polyoxyethylene sorbitan esters such as, for example,polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active substance with finely dividedsolid materials, for example talc, natural clays such as kaolin,bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be water-based or oil-based. They can beprepared for example by wet-grinding by means of customary bead mills,if appropriate with addition of surfactants, as have already been listedfor example above in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared forexample by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and, if appropriate, surfactants as havealready been mentioned for example above in the case of the otherformulation types.

Granules can be prepared either by spraying the active substance ontoadsorptive, granulated inert material or by applying active substanceconcentrates to the surface of carriers such as sand, kaolinites orgranulated inert material with the aid of stickers, for examplepolyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitableactive substances can also be granulated in the fashion which isconventional for the production of fertilizer granules, if desired as amixture with fertilizers.

Water-dispersible granules are generally prepared by customary methodssuch as spray drying, fluidized-bed granulation, disk granulation,mixing with high-speed stirrers and extrusion without solid inertmaterial.

To prepare disk granules, fluidized-bed granules, extruder granules andspray granules, see, for example methods in “Spray-Drying Handbook” 3rded. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”,Chemical and Engineering 1967, pages 147 et seq.; “Perry's ChemicalEngineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details on the formulation of crop protection products see,for example G. C. Klingman, “Weed Control as a Science”, John Wiley andSons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans,“Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications,Oxford, 1968, pages 101-103.

As a rule, the agrochemical preparations comprise 0.1 to 99% by weight,in particular 0.1 to 95% by weight, of active substance of the formula(I). In wettable powders, the active substance concentration is, forexample, approximately 10 to 90% by weight, the remainder to 100% byweight being composed of customary formulation constituents. In the caseof emulsifiable concentrates, the active substance concentration canamount to approximately 1 to 90, preferably 5 to 80% by weight.Formulations in the form of dusts comprise 1 to 30% by weight of activesubstance, preferably in most cases 5 to 20% by weight of activesubstance, and sprayable solutions comprise approximately 0.05 to 80,preferably 2 to 50% by weight of active substance. In the case ofwater-dispersible granules, the active substance content depends partlyon whether the active compound is in liquid or solid form and on thegranulation auxiliaries, fillers and the like which are being used. Inthe case of the water-dispersible granules, for example, the activesubstance content is between 1 and 95% by weight, preferably between 10and 80% by weight.

In addition, the active substance formulations mentioned comprise, ifappropriate, the auxiliaries which are conventional in each case, suchas stickers, wetters, dispersants, emulsifiers, penetrants,preservatives, antifreeze agents, solvents, fillers, carriers,colorants, antifoams, evaporation inhibitors, and pH and viscosityregulators.

Based on these formulations, it is also possible to prepare combinationswith other pesticidally active substances such as, for example,insecticides, acaricides, herbicides, fungicides, and with safeners,fertilizers and/or growth regulators, for example in the form of areadymix or a tank mix.

Active substances which can be employed in combination with the activesubstances according to the invention in mixed formulations or in thetank mix are, for example, known active substances as are described, forexample, in Weed Research 26, 441-445 (1986) or “The Pesticide Manual”,11th edition, The British Crop Protection Council and the Royal Soc. ofChemistry, 1997 and literature cited therein. Herbicides which must bementioned, and can be combined with the compounds of the formula (I),are, for example, the following active substances (note: the compoundsare either designated by the common name according to the InternationalOrganization for Standardization (ISO) or using the chemical name, ifappropriate together with a customary code number):

acetochlor; acifluorfen; aclonifen; AKH 7088, i.e.[[[1-[5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]aceticacid and its methyl ester; alachlor; alloxydim; ametryn; amidosulfuron;amitrol; AMS, i.e. ammonium sulfamate; anilofos; asulam; atrazine;azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516 H, i.e.5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluralin;benfuresate; bensulfuronmethyl; bensulide; bentazone; benzofenap;benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox;bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos;busoxinone; butachlor; butamifos; butenachlor; buthidazole; butralin;butylate; cafenstrole (CH-900); carbetamide; cafentrazone (ICI-A0051);CDM, i.e. 2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyldiethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl,chlormesulon (ICI-A0051); chlorbromuron; chlorbufam; chlorfenac;chlorflurecol-methyl; chloridazon; chlorimuron ethyl; chlornitrofen;chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron;chlorthal-dimethyl; chlorthiamid; cinmethylin; cinosulfuron; clethodim;clodinafop and its ester derivatives (for example clodinafop-propargyl);clomazone; clomeprop; cloproxydim; clopyralid; cumyluron (JC 940);cyanazine; cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron;cyhalofop and its ester derivatives (for example butylester, DEH-112);cyperquat; cyprazine; cyprazole; daimuron; 2,4-DB; dalapon; desmedipham;desmetryn; di-allate; dicamba; dichlobenil; dichlorprop; diclofop andits esters such as diclofop-methyl; diethatyl; difenoxuron; difenzoquat;diflufenican; dimefuron; dimethachlor; dimethametryn; dimethenamid(SAN-582H); dimethazone, clomazon; dimethipin; dimetrasulfuron,dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat;dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.e.5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide;endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl;ethidimuron; ethiozin; ethofumesate; F5231, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide;ethoxyfen and its esters (for example ethylester, HN-252); etobenzanid(HW 52); fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and theiresters, for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim;fenuron; flamprop-methyl; flazasulfuron; fluazifop and fluazifop-P andtheir esters, for example fluazifop-butyl and fluazifop-P-butyl;fluchloralin; flumetsulam; flumeturon; flumiclorac and its esters (forexample pentylester, S-23031); flumioxazin (S482); flumipropyn; flupoxam(KNW-739); fluorodifen; fluoroglycofen-ethyl; flupropacil (UBIC-4243);fluridone; flurochloridone; fluroxypyr; flurtamone; fomesafen; fosamine;furyloxyfen; glufosinate; glyphosate; halosafen; halosulfuron and itsesters (for example methylester, NC-319); haloxyfop and its esters;haloxyfop-P (=R-haloxyfop) and its esters; hexazinone; imazapyr;imazamethabenz-methyl; imazaquin and salts such as the ammonium salt;ioxynil; imazethamethapyr; imazethapyr; imazosulfuron; isocarbamid;isopropalin; isoproturon; isouron; isoxaben; isoxapyrifop; karbutilate;lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid;mesotrione; metamitron; metazachlor; metham; methabenzthiazuron;methazole; methoxyphenone; methyldymron; metabenzuron, methobenzuron;metobromuron; metolachlor; metosulam (XRD 511); metoxuron; metribuzin;metsulfuron-methyl; MH; molinate; monalide; monolinuron; monuron;monocarbamide dihydrogensulfate; MT 128, i.e.6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide;naproanilide; napropamide; naptalam; NC 310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neburon;nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen;norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon;oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone;phenisopham; phenmedipham; picloram; piperophos; piributicarb;pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine;prodiamine; profluralin; proglinazine-ethyl; prometon; prometryn;propachlor; propanil; propaquizafop and its esters; propazine; propham;propisochlor; propyzamide; prosulfalin; prosulfocarb; prosulfuron(CGA-152005); prynachlor; pyrazolinate; pyrazon; pyrazosulfuron-ethyl;pyrazoxyfen; pyridate; pyrithiobac (KIH-2031); pyroxofop and its esters(for example propargyl ester); quinclorac; quinmerac; quinofop and itsester derivatives, quizalofop and quizalofop-P and their esterderivatives for example quizalofop-ethyl; quizalofop-P-tefuryl and-ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, i.e.2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazole;secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e.2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoicacid and its methyl ester; suclotrione; sulfentrazon (FMC-97285,F-6285); sulfazuron; sulfometuron-methyl; sulfosate (ICI-A0224); TCA;tebutam (GCP-5544); tebuthiuron; terbacil; terbucarb; terbuchlor;terbumeton; terbuthylazine; terbutryn; TFH 450, i.e.N,N-diethyl-3-[(2-ethyl-6-methylphenyl)sulfonyl]-1H-1,2,4-triazole-1-carboxamide;thenylchlor (NSK-850); thiazafluron; thiazopyr (Mon-13200); thidiazimin(SN-24085); thiobencarb; thifensulfuron-methyl; tiocarbazil;tralkoxydim; tri-allate; triasulfuron; triazofenamide;tribenuron-methyl; triclopyr; tridiphane; trietazine; trifluralin;triflusulfuron and esters (for example methyl ester, DPX-66037);trimeturon; tsitodef; vernolate; WL 110547, i.e.5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole; UBH-509; DA89; LS82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535;DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127 andKIH-2023.

For use, the formulations, which are present in commercially availableform, are diluted in the customary manner, for example using water inthe case of wettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules. Preparations in the form of dusts, soilgranules, granules for spreading and sprayable solutions are usually notdiluted any further with other inert substances prior to use. Theapplication rate required of the compounds of the formula (I) varieswith the external conditions such as, inter alia, temperature, humidityand the nature of the herbicide used. It can vary within wide limits,for example between 0.001 and 1.0 kg/ha or more of active substance, butit is preferably between 0.005 and 750 g/ha.

The invention is illustrated by the examples below.

A. CHEMICAL EXAMPLES Preparation of2-(2-chloro-3-(3-tetrahydrofuranyl)oxymethyl-4-methylsulfonyl-benzoyl)cyclohexane-1,3-dione(Tabulated Example No. 1.1)

Step 1:2-chloro-3-(3-tetrahydrofuranyl)oxymethyl-4-methylsulfonylbenzoic acid

At 0° C., 25 ml of DMF and 3.25 g (28 mmol) of potassium tert-butoxidewere initially charged and mixed with 2.5 g (27.5 mmol) of3-hydroxytetrahydrofuran. The solution was cooled to −15° C., and 4.7 g(140 mmol) of 3-bromomethyl-2-chloro-4-methylsulfonylbenzoic acid wereadded. The mixture was then stirred at 15-20° C. for one hour. Thereaction was poured into 45 g of ice/water, acidified with 2N HCl andextracted with EA. The organic phases were dried with MgSO₄, filteredand concentrated. This gave 5.41 g of a viscous oil of a purity of about66% according to HPLC. Yield about 60%

Step 2:3-Oxo-1-cyclohexenyl-2-chloro-3-(3-tetrahydrofuranyl)oxymethyl-4-methylsulfonylbenzoate

5.41 g of crude2-chloro-3-(3-tetrahydrofuranyl)oxymethyl-4-methylsulfonylbenzoic acidwere dissolved in 30 ml of CH₂Cl₂, and 2.5 ml (28 mmol) of oxalylchloride were added slowly. The mixture was stirred for about 30 minuntil the evolution of gas had ceased. With cooling to a temperature ofbelow 15° C., the solution was added dropwise to a mixture of 2 g (17.3mmol) of 1,3-cyclohexanedione and 5 g of NEt₃ in 20 ml of CH₂Cl₂. Themixture was then stirred at RT for 1 hour. The mixture was filtered, thesolvents were removed using a rotary evaporator and 30 ml of EA werethen added to the residue. The mixture was washed initially with 5%strength HCl, then with 2% strength NaHCO₃ solution and twice withwater. The organic phase was dried using MgSO₄, filtered andconcentrated using a rotary evaporator. This gave 5 g of a highlyviscous oil which was purified chromatographically(SiO₂/_(n)-heptane:EA, 1:3). This gave 2.95 g of a colorless solid of apurity of about 99% according to HPLC.

Step 3:2-(2-Chloro-3-(3-tetrahydrofuranyl)oxymethyl-4-methylsulfonylbenzoyl)-cyclohexane-1,3-dione

8 g (18.5 mmol) of3-oxo-1-cyclohexenyl-2-chloro-3-(3-tetrahydrofuranyl)oxymethyl-4-methylsulfonylbenzoatewere suspended in 50 ml of CH₃CN, and 2.25 g (21.8 mmol) of NEt₃ and0.13 g (1.5 mmol) of acetone cyanohydrin were added with stirring. Themixture was stirred at RT for 3 hours and then concentrated using arotary evaporator. Water was added to the oily residue and the pH wasadjusted to>8 using saturated NaHCO₃ solution. The basic solution waswashed with 20 ml of EA. The aqueous solution was then acidified with 2NHCl and extracted with 2×50 ml of EA. The solution was washed withNaHCO₃ solution. The organic solution was dried with MgSO₄, filtered andconcentrated using a rotary evaporator. The product slowly crystallizedout from the concentrated solution. The solid was filtered off withsuction and washed with cold EA. This gave 6.81 g (15.9 mmol) of productof a purity of 99.8% according to HPLC and a melting point of 126° C.The yield was 85%.

The abbreviations used here denote:

-   cPr=Cyclopropyl-   nPr=n-propyl-   nBu=n-butyl-   Et=Ethyl-   Me=methyl-   Ph=Phenyl-   EA=ethyl acetate-   m.p.=melting point-   RT=room temperature

Rf=retention value TABLE 1 Compounds of the formula (I) according to theinvention in which the substituents and symbols are as defined below: R³= H Q = Q1 P = 0

No. R¹ R² X Het Physical Data 1.1 Cl SO₂Me +TC, 13 O 3-tetrahydrofuranylm.p.: 126° C. 1.2 Cl SO₂Et O 3-tetrahydrofuranyl oil, Rf = 0.2 (EA) 1.3Cl Cl O 3-tetrahydrofuranyl oil, Rf = 0.4 (EA) 1.4 Br SO₂Me O3-tetrahydrofuranyl 1.5 Br SO₂Et O 3-tetrahydrofuranyl 1.6 Br Cl O3-tetrahydrofuranyl 1.7 I SO₂Me O 3-tetrahydrofuranyl 1.8 I SO₂Et O3-tetrahydrofuranyl 1.9 I Cl O 3-tetrahydrofuranyl 1.10 Me SO₂Me O3-tetrahydrofuranyl 1.11 Me SO₂Et O 3-tetrahydrofuranyl 1.12 Me Cl O3-tetrahydrofuranyl 1.13 SMe SO₂Me O 3-tetrahydrofuranyl 1.14 SMe SO₂EtO 3-tetrahydrofuranyl 1.15 SMe Cl O 3-tetrahydrofuranyl 1.16 SO₂Me SO₂MeO 3-tetrahydrofuranyl 1.17 SO₂Me SO₂Et O 3-tetrahydrofuranyl 1.18 SO₂MeCl O 3-tetrahydrofuranyl 1.19 NO₂ SO₂Me O 3-tetrahydrofuranyl 1.20 NO₂SO₂Et O 3-tetrahydrofuranyl 1.21 NO₂ Cl O 3-tetrahydrofuranyl 1.22 OMeCl O 3-tetrahydrofuranyl oil, Rf = 0.4 (EA) 1.23 SO₂Et Cl O3-tetrahydrofuranyl 1.24 SEt Cl O 3-tetrahydrofuranyl 1.25 Cl SO₂Me O4-tetrahydropyranyl 1.26 Cl SO₂Et O 4-tetrahydropyranyl 1.27 Cl Cl O4-tetrahydropyranyl 1.28 Br SO₂Me O 4-tetrahydropyranyl 1.29 Br SO₂Et O4-tetrahydropyranyl 1.30 Br Cl O 4-tetrahydropyranyl 1.31 I SO₂Me O4-tetrahydropyranyl 1.32 I SO₂Et O 4-tetrahydropyranyl 1.33 I Cl O4-tetrahydropyranyl 1.34 Me SO₂Me O 4-tetrahydropyranyl 1.35 Me SO₂Et O4-tetrahydropyranyl 1.36 Me Cl O 4-tetrahydropyranyl 1.37 SMe SO₂Me O4-tetrahydropyranyl 1.38 SMe SO₂Et O 4-tetrahydropyranyl 1.39 SMe Cl O4-tetrahydropyranyl 1.40 SO₂Me SO₂Me O 4-tetrahydropyranyl 1.41 SO₂MeSO₂Et O 4-tetrahydropyranyl 1.42 SO₂Me Cl O 4-tetrahydropyranyl 1.43 NO₂SO₂Me O 4-tetrahydropyranyl 1.44 NO₂ SO₂Et O 4-tetrahydropyranyl 1.45NO₂ Cl O 4-tetrahydropyranyl 1.46 OMe Cl O 4-tetrahydropyranyl 1.47SO₂Et Cl O 4-tetrahydropyranyl 1.48 SEt Cl O 4-tetrahydropyranyl 1.49 ClSO₂Me O 3-tetrahydropyranyl 1.50 Cl SO₂Et O 3-tetrahydropyranyl 1.51 ClCl O 3-tetrahydropyranyl 1.52 Br SO₂Me O 3-tetrahydropyranyl 1.53 BrSO₂Et O 3-tetrahydropyranyl 1.54 Br Cl O 3-tetrahydropyranyl 1.55 ISO₂Me O 3-tetrahydropyranyl 1.56 I SO₂Et O 3-tetrahydropyranyl 1.57 I ClO 3-tetrahydropyranyl 1.58 Me SO₂Me O 3-tetrahydropyranyl 1.59 Me SO₂EtO 3-tetrahydropyranyl 1.60 Me Cl O 3-tetrahydropyranyl 1.61 SMe SO₂Me O3-tetrahydropyranyl 1.62 SMe SO₂Et O 3-tetrahydropyranyl 1.63 SMe Cl O3-tetrahydropyranyl 1.64 SO₂Me SO₂Me O 3-tetrahydropyranyl 1.65 SO₂MeSO₂Et O 3-tetrahydropyranyl 1.66 SO₂Me Cl O 3-tetrahydropyranyl 1.67 NO₂SO₂Me O 3-tetrahydropyranyl 1.68 NO₂ SO₂Et O 3-tetrahydropyranyl 1.69NO₂ Cl O 3-tetrahydropyranyl 1.70 OMe Cl O 3-tetrahydropyranyl 1.71SO₂Et Cl O 3-tetrahydropyranyl 1.72 SEt Cl O 3-tetrahydropyranyl 1.73 ClSO₂Me O 1,3-dioxan-5-yl 1.74 Cl SO₂Et O 1,3-dioxan-5-yl 1.75 Cl Cl O1,3-dioxan-5-yl 1.76 Br SO₂Me O 1,3-dioxan-5-yl 1.77 Br SO₂Et O1,3-dioxan-5-yl 1.78 Br Cl O 1,3-dioxan-5-yl 1.79 I SO₂Me O1,3-dioxan-5-yl 1.80 I SO₂Et O 1,3-dioxan-5-yl 1.81 I Cl O1,3-dioxan-5-yl 1.82 Me SO₂Me O 1,3-dioxan-5-yl 1.83 Me SO₂Et O1,3-dioxan-5-yl 1.84 Me Cl O 1,3-dioxan-5-yl 1.85 SMe SO₂Me O1,3-dioxan-5-yl 1.86 SMe SO₂Et O 1,3-dioxan-5-yl 1.87 SMe Cl O1,3-dioxan-5-yl 1.88 SO₂Me SO₂Me O 1,3-dioxan-5-yl 1.89 SO₂Me SO₂Et O1,3-dioxan-5-yl 1.90 SO₂Me Cl O 1,3-dioxan-5-yl 1.91 NO₂ SO₂Me O1,3-dioxan-5-yl 1.92 NO₂ SO₂Et O 1,3-dioxan-5-yl 1.93 NO₂ Cl O1,3-dioxan-5-yl 1.94 OMe Cl O 1,3-dioxan-5-yl 1.95 SO₂Et Cl O1,3-dioxan-5-yl 1.96 SEt Cl O 1,3-dioxan-5-yl 1.97 Cl SO₂Me Oγ-butyrolacton-2-yl oil, Rf = 0.3 (EA) 1.98 Cl SO₂Et Oγ-butyrolacton-2-yl 1.99 Cl Cl O γ-butyrolacton-2-yl 1.100 Br SO₂Me Oγ-butyrolacton-2-yl 1.101 Br SO₂Et O γ-butyrolacton-2-yl 1.102 Br Cl Oγ-butyrolacton-2-yl 1.103 I SO₂Me O γ-butyrolacton-2-yl 1.104 I SO₂Et Oγ-butyrolacton-2-yl 1.105 I Cl O γ-butyrolacton-2-yl 1.106 Me SO₂Me Oγ-butyrolacton-2-yl 1.107 Me SO₂Et O γ-butyrolacton-2-yl 1.108 Me Cl Oγ-butyrolacton-2-yl 1.109 SMe SO₂Me O γ-butyrolacton-2-yl 1.110 SMeSO₂Et O γ-butyrolacton-2-yl 1.111 SMe Cl O γ-butyrolacton-2-yl 1.112SO₂Me SO₂Me O γ-butyrolacton-2-yl 1.113 SO₂Me SO₂Et Oγ-butyrolacton-2-yl 1.114 SO₂Me Cl O γ-butyrolacton-2-yl 1.115 NO₂ SO₂MeO γ-butyrolacton-2-yl 1.116 NO₂ SO₂Et O γ-butyrolacton-2-yl 1.117 NO₂ ClO γ-butyrolacton-2-yl 1.118 OMe Cl O γ-butyrolacton-2-yl 1.119 SO₂Et ClO γ-butyrolacton-2-yl 1.120 SEt Cl O γ-butyrolacton-2-yl 1.121 Cl SO₂MeS 3-tetrahydrofuranyl 1.122 Cl SO₂Et S 3-tetrahydrofuranyl 1.123 Cl Cl S3-tetrahydrofuranyl 1.124 Br SO₂Me S 3-tetrahydrofuranyl 1.125 Br SO₂EtS 3-tetrahydrofuranyl 1.126 Br Cl S 3-tetrahydrofuranyl 1.127 I SO₂Me S3-tetrahydrofuranyl 1.128 I SO₂Et S 3-tetrahydrofuranyl 1.129 I Cl S3-tetrahydrofuranyl 1.130 Me SO₂Me S 3-tetrahydrofuranyl 1.131 Me SO₂EtS 3-tetrahydrofuranyl 1.132 Me Cl S 3-tetrahydrofuranyl 1.133 SMe SO₂MeS 3-tetrahydrofuranyl 1.134 SMe SO₂Et S 3-tetrahydrofuranyl 1.135 SMe ClS 3-tetrahydrofuranyl 1.136 SO₂Me SO₂Me S 3-tetrahydrofuranyl 1.137SO₂Me SO₂Et S 3-tetrahydrofuranyl 1.138 SO₂Me Cl S 3-tetrahydrofuranyl1.139 NO₂ SO₂Me S 3-tetrahydrofuranyl 1.140 NO₂ SO₂Et S3-tetrahydrofuranyl 1.141 NO₂ Cl S 3-tetrahydrofuranyl 1.142 OMe Cl S3-tetrahydrofuranyl 1.143 SO₂Et Cl S 3-tetrahydrofuranyl 1.144 SEt Cl S3-tetrahydrofuranyl 1.145 Cl SO₂Me S 4-tetrahydropyranyl 1.146 Cl SO₂EtS 4-tetrahydropyranyl 1.147 Cl Cl S 4-tetrahydropyranyl 1.148 Br SO₂Me S4-tetrahydropyranyl 1.149 Br SO₂Et S 4-tetrahydropyranyl 1.150 Br Cl S4-tetrahydropyranyl 1.151 I SO₂Me S 4-tetrahydropyranyl 1.152 I SO₂Et S4-tetrahydropyranyl 1.153 I Cl S 4-tetrahydropyranyl 1.154 Me SO₂Me S4-tetrahydropyranyl 1.155 Me SO₂Et S 4-tetrahydropyranyl 1.156 Me Cl S4-tetrahydropyranyl 1.157 SMe SO₂Me S 4-tetrahydropyranyl 1.158 SMeSO₂Et S 4-tetrahydropyranyl 1.159 SMe Cl S 4-tetrahydropyranyl 1.160SO₂Me SO₂Me S 4-tetrahydropyranyl 1.161 SO₂Me SO₂Et S4-tetrahydropyranyl 1.162 SO₂Me Cl S 4-tetrahydropyranyl 1.163 NO₂ SO₂MeS 4-tetrahydropyranyl 1.164 NO₂ SO₂Et S 4-tetrahydropyranyl 1.165 NO₂ ClS 4-tetrahydropyranyl 1.166 Ome Cl S 4-tetrahydropyranyl 1.167 SO₂Et ClS 4-tetrahydropyranyl 1.168 SEt Cl S 4-tetrahydropyranyl 1.169 Cl SO₂MeS 3-tetrahydropyranyl 1.170 Cl SO₂Et S 3-tetrahydropyranyl 1.171 Cl Cl S3-tetrahydropyranyl 1.172 Br SO₂Me S 3-tetrahydropyranyl 1.173 Br SO₂EtS 3-tetrahydropyranyl 1.174 Br Cl S 3-tetrahydropyranyl 1.175 I SO₂Me S3-tetrahydropyranyl 1.176 I SO₂Et S 3-tetrahydropyranyl 1.177 I Cl S3-tetrahydropyranyl 1.178 Me SO₂Me S 3-tetrahydropyranyl 1.179 Me SO₂EtS 3-tetrahydropyranyl 1.180 Me Cl S 3-tetrahydropyranyl 1.181 SMe SO₂MeS 3-tetrahydropyranyl 1.182 SMe SO₂Et S 3-tetrahydropyranyl 1.183 SMe ClS 3-tetrahydropyranyl 1.184 SO₂Me SO₂Me S 3-tetrahydropyranyl 1.185SO₂Me SO₂Et S 3-tetrahydropyranyl 1.186 SO₂Me Cl S 3-tetrahydropyranyl1.187 NO₂ SO₂Me S 3-tetrahydropyranyl 1.188 NO₂ SO₂Et S3-tetrahydropyranyl 1.189 NO₂ Cl S 3-tetrahydropyranyl 1.190 OMe Cl S3-tetrahydropyranyl 1.191 SO₂Et Cl S 3-tetrahydropyranyl 1.192 SEt Cl S3-tetrahydropyranyl 1.193 Cl SO₂Me S 1,3-dioxan-5-yl 1.194 Cl SO₂Et S1,3-dioxan-5-yl 1.195 Cl Cl S 1,3-dioxan-5-yl 1.196 Br SO₂Me S1,3-dioxan-5-yl 1.197 Br SO₂Et S 1,3-dioxan-5-yl 1.198 Br Cl S1,3-dioxan-5-yl 1.199 I SO₂Me S 1,3-dioxan-5-yl 1.200 I SO₂Et S1,3-dioxan-5-yl 1.201 I Cl S 1,3-dioxan-5-yl 1.202 Me SO₂Me S1,3-dioxan-5-yl 1.203 Me SO₂Et S 1,3-dioxan-5-yl 1.204 Me Cl S1,3-dioxan-5-yl 1.205 SMe SO₂Me S 1,3-dioxan-5-yl 1.206 SMe SO₂Et S1,3-dioxan-5-yl 1.207 SMe Cl S 1,3-dioxan-5-yl 1.208 SO₂Me SO₂Me S1,3-dioxan-5-yl 1.209 SO₂Me SO₂Et S 1,3-dioxan-5-yl 1.210 SO₂Me Cl S1,3-dioxan-5-yl 1.211 NO₂ SO₂Me S 1,3-dioxan-5-yl 1.212 NO₂ SO₂Et S1,3-dioxan-5-yl 1.213 NO₂ Cl S 1,3-dioxan-5-yl 1.214 OMe Cl S1,3-dioxan-5-yl 1.215 SO₂Et Cl S 1,3-dioxan-5-yl 1.216 SEt Cl S1,3-dioxan-5-yl 1.217 Cl SO₂Me S γ-butyrolacton-2-yl 1.218 Cl SO₂Et Sγ-butyrolacton-2-yl 1.219 Cl Cl S γ-butyrolacton-2-yl 1.220 Br SO₂Me Sγ-butyrolacton-2-yl 1.221 Br SO₂Et S γ-butyrolacton-2-yl 1.222 Br Cl Sγ-butyrolacton-2-yl 1.223 I SO₂Me S γ-butyrolacton-2-yl 1.224 I SO₂Et Sγ-butyrolacton-2-yl 1.225 I Cl S γ-butyrolacton-2-yl 1.226 Me SO₂Me Sγ-butyrolacton-2-yl 1.227 Me SO₂Et S γ-butyrolacton-2-yl 1.228 Me Cl Sγ-butyrolacton-2-yl 1.229 SMe SO₂Me S γ-butyrolacton-2-yl 1.220 SMeSO₂Et S γ-butyrolacton-2-yl 1.231 SMe Cl S γ-butyrolacton-2-yl 1.232SO₂Me SO₂Me S γ-butyrolacton-2-yl 1.233 SO₂Me SO₂Et Sγ-butyrolacton-2-yl 1.234 SO₂Me Cl S γ-butyrolacton-2-yl 1.235 NO₂ SO₂MeS γ-butyrolacton-2-yl 1.236 NO₂ SO₂Et S γ-butyrolacton-2-yl 1.237 NO₂ ClS γ-butyrolacton-2-yl 1.238 OMe Cl S γ-butyrolacton-2-yl 1.239 SO₂Et ClS γ-butyrolacton-2-yl 1.240 SEt Cl S γ-butyrolacton-2-yl 1.241 OEt Cl O3-tetrahydrofuranyl oil, Rf = 0.4 (EA)

TABLE 2 Compounds of the formula (I) according to the invention in whichthe substituents and symbols are as defined below: R³ = H Q = Q1 p = 2

No. R¹ R² X Het Physical Data 2.1 Cl SO₂Me O 3-tetrahydrofuranyl oil, Rf= 0.2 (EA) 2.2 Cl SO₂Et O 3-tetrahydrofuranyl oil, Rf = 0.4 (EA) 2.3 ClCl O 3-tetrahydrofuranyl 2.4 Br SO₂Me O 3-tetrahydrofuranyl 2.5 Br SO₂EtO 3-tetrahydrofuranyl 2.6 Br Cl O 3-tetrahydrofuranyl 2.7 I SO₂Me O3-tetrahydrofuranyl 2.8 I SO₂Et O 3-tetrahydrofuranyl 2.9 I Cl O3-tetrahydrofuranyl 2.10 Me SO₂Me O 3-tetrahydrofuranyl 2.11 Me SO₂Et O3-tetrahydrofuranyl 2.12 Me Cl O 3-tetrahydrofuranyl 2.13 SMe SO₂Me O3-tetrahydrofuranyl 2.14 SMe SO₂Et O 3-tetrahydrofuranyl 2.15 SMe Cl O3-tetrahydrofuranyl 2.16 SO₂Me SO₂Me O 3-tetrahydrofuranyl 2.17 SO₂MeSO₂Et O 3-tetrahydrofuranyl 2.18 SO₂Me Cl O 3-tetrahydrofuranyl 2.19 NO₂SO₂Me O 3-tetrahydrofuranyl 2.20 NO₂ SO₂Et O 3-tetrahydrofuranyl 2.21NO₂ Cl O 3-tetrahydrofuranyl 2.22 Cl SO₂Me O 4-tetrahydropyranyl 2.23 ClSO₂Et O 4-tetrahydropyranyl 2.24 Cl Cl O 4-tetrahydropyranyl 2.25 BrSO₂Me O 4-tetrahydropyranyl 2.26 Br SO₂Et O 4-tetrahydropyranyl 2.27 BrCl O 4-tetrahydropyranyl 2.28 I SO₂Me O 4-tetrahydropyranyl 2.29 I SO₂EtO 4-tetrahydropyranyl 2.30 I Cl O 4-tetrahydropyranyl 2.31 Me SO₂Me O4-tetrahydropyranyl 2.32 Me SO₂Et O 4-tetrahydropyranyl 2.33 Me Cl O4-tetrahydropyranyl 2.34 SMe SO₂Me O 4-tetrahydropyranyl 2.35 SMe SO₂EtO 4-tetrahydropyranyl 2.36 SMe Cl O 4-tetrahydropyranyl 2.37 SO₂Me SO₂MeO 4-tetrahydropyranyl 2.38 SO₂Me SO₂Et O 4-tetrahydropyranyl 2.39 SO₂MeCl O 4-tetrahydropyranyl 2.40 NO₂ SO₂Me O 4-tetrahydropyranyl 2.41 NO₂SO₂Et O 4-tetrahydropyranyl 2.42 NO₂ Cl O 4-tetrahydropyranyl 2.43 ClSO₂Me O 3-tetrahydropyranyl 2.44 Cl SO₂Et O 3-tetrahydropyranyl 2.45 ClCl O 3-tetrahydropyranyl 2.46 Br SO₂Me O 3-tetrahydropyranyl 2.47 BrSO₂Et O 3-tetrahydropyranyl 2.48 Br Cl O 3-tetrahydropyranyl 2.49 ISO₂Me O 3-tetrahydropyranyl 2.50 I SO₂Et O 3-tetrahydropyranyl 2.51 I ClO 3-tetrahydropyranyl 2.52 Me SO₂Me O 3-tetrahydropyranyl 2.53 Me SO₂EtO 3-tetrahydropyranyl 2.54 Me Cl O 3-tetrahydropyranyl 2.55 SMe SO₂Me O3-tetrahydropyranyl 2.56 SMe SO₂Et O 3-tetrahydropyranyl 2.57 SMe Cl O3-tetrahydropyranyl 2.58 SO₂Me SO₂Me O 3-tetrahydropyranyl 2.59 SO₂MeSO₂Et O 3-tetrahydropyranyl 2.60 SO₂Me Cl O 3-tetrahydropyranyl 2.61 NO₂SO₂Me O 3-tetrahydropyranyl 2.62 NO₂ SO₂Et O 3-tetrahydropyranyl 2.63NO₂ Cl O 3-tetrahydropyranyl 2.64 Cl SO₂Me O 1,3-dioxan-5-yl 2.65 ClSO₂Et O 1,3-dioxan-5-yl 2.66 Cl Cl O 1,3-dioxan-5-yl 2.67 Br SO₂Me O1,3-dioxan-5-yl 2.68 Br SO₂Et O 1,3-dioxan-5-yl 2.69 Br Cl O1,3-dioxan-5-yl 2.70 I SO₂Me O 1,3-dioxan-5-yl 2.71 I SO₂Et O1,3-dioxan-5-yl 2.72 I Cl O 1,3-dioxan-5-yl 2.73 Me SO₂Me O1,3-dioxan-5-yl 2.74 Me SO₂Et O 1,3-dioxan-5-yl 2.75 Me Cl O1,3-dioxan-5-yl 2.76 SMe SO₂Me O 1,3-dioxan-5-yl 2.77 SMe SO₂Et O1,3-dioxan-5-yl 2.78 SMe Cl O 1,3-dioxan-5-yl 2.79 SO₂Me SO₂Me O1,3-dioxan-5-yl 2.80 SO₂Me SO₂Et O 1,3-dioxan-5-yl 2.81 SO₂Me Cl O1,3-dioxan-5-yl 2.82 NO₂ SO₂Me O 1,3-dioxan-5-yl 2.83 NO₂ SO₂Et O1,3-dioxan-5-yl 2.84 NO₂ Cl O 1,3-dioxan-5-yl 2.85 Cl SO₂Me Oγ-butyrolacton-2-yl 2.86 Cl SO₂Et O γ-butyrolacton-2-yl 2.87 Cl Cl Oγ-butyrolacton-2-yl 2.88 Br SO₂Me O γ-butyrolacton-2-yl 2.89 Br SO₂Et Oγ-butyrolacton-2-yl 2.90 Br Cl O γ-butyrolacton-2-yl 2.91 I SO₂Me Oγ-butyrolacton-2-yl 2.92 I SO₂Et O γ-butyrolacton-2-yl 2.93 I Cl Oγ-butyrolacton-2-yl 2.94 Me SO₂Me O γ-butyrolacton-2-yl 2.95 Me SO₂Et Oγ-butyrolacton-2-yl 2.96 Me Cl O γ-butyrolacton-2-yl 2.97 SMe SO₂Me Oγ-butyrolacton-2-yl 2.98 SMe SO₂Et O γ-butyrolacton-2-yl 2.99 SMe Cl Oγ-butyrolacton-2-yl 2.100 SO₂Me SO₂Me O γ-butyrolacton-2-yl 2.101 SO₂MeSO₂Et O γ-butyrolacton-2-yl 2.102 SO₂Me Cl O γ-butyrolacton-2-yl 2.103NO₂ SO₂Me O γ-butyrolacton-2-yl 2.104 NO₂ SO₂Et O γ-butyrolacton-2-yl2.105 NO₂ Cl O γ-butyrolacton-2-yl 2.106 Cl SO₂Me S 3-tetrahydrofuranyl2.107 Cl SO₂Et S 3-tetrahydrofuranyl 2.108 Cl Cl S 3-tetrahydrofuranyl2.109 Br SO₂Me S 3-tetrahydrofuranyl 2.110 Br SO₂Et S3-tetrahydrofuranyl 2.111 Br Cl S 3-tetrahydrofuranyl 2.112 I SO₂Me S3-tetrahydrofuranyl 2.113 I SO₂Et S 3-tetrahydrofuranyl 2.114 I Cl S3-tetrahydrofuranyl 2.115 Me SO₂Me S 3-tetrahydrofuranyl 2.116 Me SO₂EtS 3-tetrahydrofuranyl 2.117 Me Cl S 3-tetrahydrofuranyl 2.118 SMe SO₂MeS 3-tetrahydrofuranyl 2.119 SMe SO₂Et S 3-tetrahydrofuranyl 2.120 SMe ClS 3-tetrahydrofuranyl 2.121 SO₂Me SO₂Me S 3-tetrahydrofuranyl 2.122SO₂Me SO₂Et S 3-tetrahydrofuranyl 2.123 SO₂Me Cl S 3-tetrahydrofuranyl2.124 NO₂ SO₂Me S 3-tetrahydrofuranyl 2.125 NO₂ SO₂Et S3-tetrahydrofuranyl 2.126 NO₂ Cl S 3-tetrahydrofuranyl 2.127 Cl SO₂Me S4-tetrahydropyranyl 2.128 Cl SO₂Et S 4-tetrahydropyranyl 2.129 Cl Cl S4-tetrahydropyranyl 2.130 Br SO₂Me S 4-tetrahydropyranyl 2.131 Br SO₂EtS 4-tetrahydropyranyl 2.132 Br Cl S 4-tetrahydropyranyl 2.133 I SO₂Me S4-tetrahydropyranyl 2.134 I SO₂Et S 4-tetrahydropyranyl 2.135 I Cl S4-tetrahydropyranyl 2.136 Me SO₂Me S 4-tetrahydropyranyl 2.137 Me SO₂EtS 4-tetrahydropyranyl 2.138 Me Cl S 4-tetrahydropyranyl 2.139 SMe SO₂MeS 4-tetrahydropyranyl 2.140 SMe SO₂Et S 4-tetrahydropyranyl 2.141 SMe ClS 4-tetrahydropyranyl 2.142 SO₂Me SO₂Me S 4-tetrahydropyranyl 2.143SO₂Me SO₂Et S 4-tetrahydropyranyl 2.144 SO₂Me Cl S 4-tetrahydropyranyl2.145 NO₂ SO₂Me S 4-tetrahydropyranyl 2.146 NO₂ SO₂Et S4-tetrahydropyranyl 2.147 NO₂ Cl S 4-tetrahydropyranyl 2.148 Cl SO₂Me S3-tetrahydropyranyl 2.149 Cl SO₂Et S 3-tetrahydropyranyl 2.150 Cl Cl S3-tetrahydropyranyl 2.151 Br SO₂Me S 3-tetrahydropyranyl 2.152 Br SO₂EtS 3-tetrahydropyranyl 2.153 Br Cl S 3-tetrahydropyranyl 2.154 I SO₂Me S3-tetrahydropyranyl 2.155 I SO₂Et S 3-tetrahydropyranyl 2.156 I Cl S3-tetrahydropyranyl 2.157 Me SO₂Me S 3-tetrahydropyranyl 2.158 Me SO₂EtS 3-tetrahydropyranyl 2.159 Me Cl S 3-tetrahydropyranyl 2.160 SMe SO₂MeS 3-tetrahydropyranyl 2.161 SMe SO₂Et S 3-tetrahydropyranyl 2.162 SMe ClS 3-tetrahydropyranyl 2.163 SO₂Me SO₂Me S 3-tetrahydropyranyl 2.164SO₂Me SO₂Et S 3-tetrahydropyranyl 2.165 SO₂Me Cl S 3-tetrahydropyranyl2.166 NO₂ SO₂Me S 3-tetrahydropyranyl 2.167 NO₂ SO₂Et S3-tetrahydropyranyl 2.168 NO₂ Cl S 3-tetrahydropyranyl 2.169 Cl SO₂Me S1,3-dioxan-5-yl 2.170 Cl SO₂Et S 1,3-dioxan-5-yl 2.171 Cl Cl S1,3-dioxan-5-yl 2.172 Br SO₂Me S 1,3-dioxan-5-yl 2.173 Br SO₂Et S1,3-dioxan-5-yl 2.174 Br Cl S 1,3-dioxan-5-yl 2.175 I SO₂Me S1,3-dioxan-5-yl 2.176 I SO₂Et S 1,3-dioxan-5-yl 2.177 I Cl S1,3-dioxan-5-yl 2.178 Me SO₂Me S 1,3-dioxan-5-yl 2.179 Me SO₂Et S1,3-dioxan-5-yl 2.180 Me Cl S 1,3-dioxan-5-yl 2.181 SMe SO₂Me S1,3-dioxan-5-yl 2.182 SMe SO₂Et S 1,3-dioxan-5-yl 2.183 SMe Cl S1,3-dioxan-5-yl 2.184 SO₂Me SO₂Me S 1,3-dioxan-5-yl 2.185 SO₂Me SO₂Et S1,3-dioxan-5-yl 2.186 SO₂Me Cl S 1,3-dioxan-5-yl 2.187 NO₂ SO₂Me S1,3-dioxan-5-yl 2.188 NO₂ SO₂Et S 1,3-dioxan-5-yl 2.189 NO₂ Cl S1,3-dioxan-5-yl 2.190 Cl SO₂Me S γ-butyrolacton-2-yl 2.191 Cl SO₂Et Sγ-butyrolacton-2-yl 2.192 Cl Cl S γ-butyrolacton-2-yl 2.193 Br SO₂Me Sγ-butyrolacton-2-yl 2.194 Br SO₂Et S γ-butyrolacton-2-yl 2.195 Br Cl Sγ-butyrolacton-2-yl 2.196 I SO₂Me S γ-butyrolacton-2-yl 2.197 I SO₂Et Sγ-butyrolacton-2-yl 2.198 I Cl S γ-butyrolacton-2-yl 2.199 Me SO₂Me Sγ-butyrolacton-2-yl 2.200 Me SO₂Et S γ-butyrolacton-2-yl 2.201 Me Cl Sγ-butyrolacton-2-yl 2.202 SMe SO₂Me S γ-butyrolacton-2-yl 2.203 SMeSO₂Et S γ-butyrolacton-2-yl 2.204 SMe Cl S γ-butyrolacton-2-yl 2.205SO₂Me SO₂Me S γ-butyrolacton-2-yl 2.206 SO₂Me SO₂Et Sγ-butyrolacton-2-yl 2.207 SO₂Me Cl S γ-butyrolacton-2-yl 2.208 NO₂ SO₂MeS γ-butyrolacton-2-yl 2.209 NO₂ SO₂Et S γ-butyrolacton-2-yl 2.210 NO₂ ClS γ-butyrolacton-2-yl 2.211 SEt Cl S 3-tetrahydrofuranyl 2.212 SEt Cl S3-tetrahydropyranyl 2.213 SEt Cl S 4-tetrahydropyranyl 2.214 SEt Cl S1,3-dioxan-5-yl 2.215 SEt Cl S γ-butyrolacton-2-yl 2.216 SO₂Et Cl S3-tetrahydrofuranyl 2.217 SO₂Et Cl S 3-tetrahydropyranyl 2.218 SO₂Et ClS 4-tetrahydropyranyl 2.219 SO₂Et Cl S 1,3-dioxan-5-yl 2.220 SO₂Et Cl Sγ-butyrolacton-2-yl 2.221 OMe Cl S 3-tetrahydrofuranyl 2.222 OMe Cl S3-tetrahydropyranyl 2.223 OMe Cl S 4-tetrahydropyranyl 2.224 OMe Cl S1,3-dioxan-5-yl 2.225 OMe Cl S γ-butyrolacton-2-yl

TABLE 3 Compounds of the formula (I) according to the invention in whichthe substituents and symbols are as defined below: R³ = H Q = Q1 p = 2

No. R¹ R² X Het Physical Data 3.1 Cl SO₂Me O 3-tetrahydrofuranyl oil, Rf= 0.2 (EA) 3.2 Cl SO₂Et O 3-tetrahydrofuranyl oil, Rf = 0.2 (EA) 3.3 ClCl O 3-tetrahydrofuranyl 3.4 Br SO₂Me O 3-tetrahydrofuranyl 3.5 Br SO₂EtO 3-tetrahydrofuranyl 3.6 Br Cl O 3-tetrahydrofuranyl 3.7 I SO₂Me O3-tetrahydrofuranyl 3.8 I SO₂Et O 3-tetrahydrofuranyl 3.9 I Cl O3-tetrahydrofuranyl 3.10 Me SO₂Me O 3-tetrahydrofuranyl 3.11 Me SO₂Et O3-tetrahydrofuranyl 3.12 Me Cl O 3-tetrahydrofuranyl 3.13 SMe SO₂Me O3-tetrahydrofuranyl 3.14 SMe SO₂Et O 3-tetrahydrofuranyl 3.15 SMe Cl O3-tetrahydrofuranyl 3.16 SO₂Me SO₂Me O 3-tetrahydrofuranyl 3.17 SO₂MeSO₂Et O 3-tetrahydrofuranyl 3.18 SO₂Me Cl O 3-tetrahydrofuranyl 3.19 NO₂SO₂Me O 3-tetrahydrofuranyl 3.20 NO₂ SO₂Et O 3-tetrahydrofuranyl 3.21NO₂ Cl O 3-tetrahydrofuranyl 3.22 Cl SO₂Me O 4-tetrahydropyranyl 3.23 ClSO₂Et O 4-tetrahydropyranyl 3.24 Cl Cl O 4-tetrahydropyranyl 3.25 BrSO₂Me O 4-tetrahydropyranyl 3.26 Br SO₂Et O 4-tetrahydropyranyl 3.27 BrCl O 4-tetrahydropyranyl 3.28 I SO₂Me O 4-tetrahydropyranyl 3.29 I SO₂EtO 4-tetrahydropyranyl 3.30 I Cl O 4-tetrahydropyranyl 3.31 Me SO₂Me O4-tetrahydropyranyl 3.32 Me SO₂Et O 4-tetrahydropyranyl 3.33 Me Cl O4-tetrahydropyranyl 3.34 SMe SO₂Me O 4-tetrahydropyranyl 3.35 SMe SO₂EtO 4-tetrahydropyranyl 3.36 SMe Cl O 4-tetrahydropyranyl 3.37 SO₂Me SO₂MeO 4-tetrahydropyranyl 3.38 SO₂Me SO₂Et O 4-tetrahydropyranyl 3.39 SO₂MeCl O 4-tetrahydropyranyl 3.40 NO₂ SO₂Me O 4-tetrahydropyranyl 3.41 NO₂SO₂Et O 4-tetrahydropyranyl 3.42 NO₂ Cl O 4-tetrahydropyranyl 3.43 ClSO₂Me O 3-tetrahydropyranyl 3.44 Cl SO₂Et O 3-tetrahydropyranyl 3.45 ClCl O 3-tetrahydropyranyl 3.46 Br SO₂Me O 3-tetrahydropyranyl 3.47 BrSO₂Et O 3-tetrahydropyranyl 3.48 Br Cl O 3-tetrahydropyranyl 3.49 ISO₂Me O 3-tetrahydropyranyl 3.50 I SO₂Et O 3-tetrahydropyranyl 3.51 I ClO 3-tetrahydropyranyl 3.52 Me SO₂Me O 3-tetrahydropyranyl 3.53 Me SO₂EtO 3-tetrahydropyranyl 3.54 Me Cl O 3-tetrahydropyranyl 3.55 SMe SO₂Me O3-tetrahydropyranyl 3.56 SMe SO₂Et O 3-tetrahydropyranyl 3.57 SMe Cl O3-tetrahydropyranyl 3.58 SO₂Me SO₂Me O 3-tetrahydropyranyl 3.59 SO₂MeSO₂Et O 3-tetrahydropyranyl 3.60 SO₂Me Cl O 3-tetrahydropyranyl 3.61 NO₂SO₂Me O 3-tetrahydropyranyl 3.62 NO₂ SO₂Et O 3-tetrahydropyranyl 3.63NO₂ Cl O 3-tetrahydropyranyl 3.64 Cl SO₂Me O 1,3-dioxan-5-yl 3.65 ClSO₂Et O 1,3-dioxan-5-yl 3.66 Cl Cl O 1,3-dioxan-5-yl 3.67 Br SO₂Me O1,3-dioxan-5-yl 3.68 Br SO₂Et O 1,3-dioxan-5-yl 3.69 Br Cl O1,3-dioxan-5-yl 3.70 I SO₂Me O 1,3-dioxan-5-yl 3.71 I SO₂Et O1,3-dioxan-5-yl 3.72 I Cl O 1,3-dioxan-5-yl 3.73 Me SO₂Me O1,3-dioxan-5-yl 3.74 Me SO₂Et O 1,3-dioxan-5-yl 3.75 Me Cl O1,3-dioxan-5-yl 3.76 SMe SO₂Me O 1,3-dioxan-5-yl 3.77 SMe SO₂Et O1,3-dioxan-5-yl 3.78 SMe Cl O 1,3-dioxan-5-yl 3.79 SO₂Me SO₂Me O1,3-dioxan-5-yl 3.80 SO₂Me SO₂Et O 1,3-dioxan-5-yl 3.81 SO₂Me Cl O1,3-dioxan-5-yl 3.82 NO₂ SO₂Me O 1,3-dioxan-5-yl 3.83 NO₂ SO₂Et O1,3-dioxan-5-yl 3.84 NO₂ Cl O 1,3-dioxan-5-yl 3.85 Cl SO₂Me Oγ-butyrolacton-2-yl 3.86 Cl SO₂Et O γ-butyrolacton-2-yl 3.87 Cl Cl Oγ-butyrolacton-2-yl 3.88 Br SO₂Me O γ-butyrolacton-2-yl 3.89 Br SO₂Et Oγ-butyrolacton-2-yl 3.90 Br Cl O γ-butyrolacton-2-yl 3.91 I SO₂Me Oγ-butyrolacton-2-yl 3.92 I SO₂Et O γ-butyrolacton-2-yl 3.93 I Cl Oγ-butyrolacton-2-yl 3.94 Me SO₂Me O γ-butyrolacton-2-yl 3.95 Me SO₂Et Oγ-butyrolacton-2-yl 3.96 Me Cl O γ-butyrolacton-2-yl 3.97 SMe SO₂Me Oγ-butyrolacton-2-yl 3.98 SMe SO₂Et O γ-butyrolacton-2-yl 3.99 SMe Cl Oγ-butyrolacton-2-yl 3.100 SO₂Me SO₂Me O γ-butyrolacton-2-yl 3.101 SO₂MeSO₂Et O γ-butyrolacton-2-yl 3.102 SO₂Me Cl O γ-butyrolacton-2-yl 3.103NO₂ SO₂Me O γ-butyrolacton-2-yl 3.104 NO₂ SO₂Et O γ-butyrolacton-2-yl3.105 NO₂ Cl O γ-butyrolacton-2-yl 3.106 Cl SO₂Me S 3-tetrahydrofuranyl3.107 Cl SO₂Et S 3-tetrahydrofuranyl 3.108 Cl Cl S 3-tetrahydrofuranyl3.109 Br SO₂Me S 3-tetrahydrofuranyl 3.110 Br SO₂Et S3-tetrahydrofuranyl 3.111 Br Cl S 3-tetrahydrofuranyl 3.112 I SO₂Me S3-tetrahydrofuranyl 3.113 I SO₂Et S 3-tetrahydrofuranyl 3.114 I Cl S3-tetrahydrofuranyl 3.115 Me SO₂Me S 3-tetrahydrofuranyl 3.116 Me SO₂EtS 3-tetrahydrofuranyl 3.117 Me Cl S 3-tetrahydrofuranyl 3.118 SMe SO₂MeS 3-tetrahydrofuranyl 3.119 SMe SO₂Et S 3-tetrahydrofuranyl 3.120 SMe ClS 3-tetrahydrofuranyl 3.121 SO₂Me SO₂Me S 3-tetrahydrofuranyl 3.122SO₂Me SO₂Et S 3-tetrahydrofuranyl 3.123 SO₂Me Cl S 3-tetrahydrofuranyl3.124 NO₂ SO₂Me S 3-tetrahydrofuranyl 3.125 NO₂ SO₂Et S3-tetrahydrofuranyl 3.126 NO₂ Cl S 3-tetrahydrofuranyl 3.127 Cl SO₂Me S4-tetrahydropyranyl 3.128 Cl SO₂Et S 4-tetrahydropyranyl 3.129 Cl Cl S4-tetrahydropyranyl 3.130 Br SO₂Me S 4-tetrahydropyranyl 3.131 Br SO₂EtS 4-tetrahydropyranyl 3.132 Br Cl S 4-tetrahydropyranyl 3.133 I SO₂Me S4-tetrahydropyranyl 3.134 I SO₂Et S 4-tetrahydropyranyl 3.135 I Cl S4-tetrahydropyranyl 3.136 Me SO₂Me S 4-tetrahydropyranyl 3.137 Me SO₂EtS 4-tetrahydropyranyl 3.138 Me Cl S 4-tetrahydropyranyl 3.139 SMe SO₂MeS 4-tetrahydropyranyl 3.140 SMe SO₂Et S 4-tetrahydropyranyl 3.141 SMe ClS 4-tetrahydropyranyl 3.142 SO₂Me SO₂Me S 4-tetrahydropyranyl 3.143SO₂Me SO₂Et S 4-tetrahydropyranyl 3.144 SO₂Me Cl S 4-tetrahydropyranyl3.145 NO₂ SO₂Me S 4-tetrahydropyranyl 3.146 NO₂ SO₂Et S4-tetrahydropyranyl 3.147 NO₂ Cl S 4-tetrahydropyranyl 3.148 Cl SO₂Me S3-tetrahydropyranyl 3.149 Cl SO₂Et S 3-tetrahydropyranyl 3.150 Cl Cl S3-tetrahydropyranyl 3.151 Br SO₂Me S 3-tetrahydropyranyl 3.152 Br SO₂EtS 3-tetrahydropyranyl 3.153 Br Cl S 3-tetrahydropyranyl 3.154 I SO₂Me S3-tetrahydropyranyl 3.155 I SO₂Et S 3-tetrahydropyranyl 3.156 I Cl S3-tetrahydropyranyl 3.157 Me SO₂Me S 3-tetrahydropyranyl 3.158 Me SO₂EtS 3-tetrahydropyranyl 3.159 Me Cl S 3-tetrahydropyranyl 3.160 SMe SO₂MeS 3-tetrahydropyranyl 3.161 SMe SO₂Et S 3-tetrahydropyranyl 3.162 SMe ClS 3-tetrahydropyranyl 3.163 SO₂Me SO₂Me S 3-tetrahydropyranyl 3.164SO₂Me SO₂Et S 3-tetrahydropyranyl 3.165 SO₂Me Cl S 3-tetrahydropyranyl3.166 NO₂ SO₂Me S 3-tetrahydropyranyl 3.167 NO₂ SO₂Et S3-tetrahydropyranyl 3.168 NO₂ Cl S 3-tetrahydropyranyl 3.169 Cl SO₂Me S1,3-dioxan-5-yl 3.170 Cl SO₂Et S 1,3-dioxan-5-yl 3.171 Cl Cl S1,3-dioxan-5-yl 3.172 Br SO₂Me S 1,3-dioxan-5-yl 3.173 Br SO₂Et S1,3-dioxan-5-yl 3.174 Br Cl S 1,3-dioxan-5-yl 3.175 I SO₂Me S1,3-dioxan-5-yl 3.176 I SO₂Et S 1,3-dioxan-5-yl 3.177 I Cl S1,3-dioxan-5-yl 3.178 Me SO₂Me S 1,3-dioxan-5-yl 3.179 Me SO₂Et S1,3-dioxan-5-yl 3.180 Me Cl S 1,3-dioxan-5-yl 3.181 SMe SO₂Me S1,3-dioxan-5-yl 3.182 SMe SO₂Et S 1,3-dioxan-5-yl 3.183 SMe Cl S1,3-dioxan-5-yl 3.184 SO₂Me SO₂Me S 1,3-dioxan-5-yl 3.185 SO₂Me SO₂Et S1,3-dioxan-5-yl 3.186 SO₂Me Cl S 1,3-dioxan-5-yl 3.187 NO₂ SO₂Me S1,3-dioxan-5-yl 3.188 NO₂ SO₂Et S 1,3-dioxan-5-yl 3.189 NO₂ Cl S1,3-dioxan-5-yl 3.190 Cl SO₂Me S γ-butyrolacton-2-yl 3.191 Cl SO₂Et Sγ-butyrolacton-2-yl 3.192 Cl Cl S γ-butyrolacton-2-yl 3.193 Br SO₂Me Sγ-butyrolacton-2-yl 3.194 Br SO₂Et S γ-butyrolacton-2-yl 3.195 Br Cl Sγ-butyrolacton-2-yl 3.196 I SO₂Me S γ-butyrolacton-2-yl 3.197 I SO₂Et Sγ-butyrolacton-2-yl 3.198 I Cl S γ-butyrolacton-2-yl 3.199 Me SO₂Me Sγ-butyrolacton-2-yl 3.200 Me SO₂Et S γ-butyrolacton-2-yl 3.201 Me Cl Sγ-butyrolacton-2-yl 3.202 SMe SO₂Me S γ-butyrolacton-2-yl 3.203 SMeSO₂Et S γ-butyrolacton-2-yl 3.204 SMe Cl S γ-butyrolacton-2-yl 3.205SO₂Me SO₂Me S γ-butyrolacton-2-yl 3.206 SO₂Me SO₂Et Sγ-butyrolacton-2-yl 3.207 SO₂Me Cl S γ-butyrolacton-2-yl 3.208 NO₂ SO₂MeS γ-butyrolacton-2-yl 3.209 NO₂ SO₂Et S γ-butyrolacton-2-yl 3.210 NO₂ ClS γ-butyrolacton-2-yl

TABLE 4 Compounds of the formula (I) according to the invention in whichthe substituents and symbols are as defined below: R³ = H Q = Q2 R⁶ = MeR⁷ = Me R⁸ = H

No. R¹ R² X Het Physical Data 4.1 Cl SO₂Me O 3-tetrahydrofuranyl oil, Rf= 0.1 (EA) 4.2 Cl SO₂Et O 3-tetrahydrofuranyl oil, Rf = 0.1 (EA) 4.3 ClCl O 3-tetrahydrofuranyl 4.4 Br SO₂Me O 3-tetrahydrofuranyl 4.5 Br SO₂EtO 3-tetrahydrofuranyl 4.6 Br Cl O 3-tetrahydrofuranyl 4.7 I SO₂Me O3-tetrahydrofuranyl 4.8 I SO₂Et O 3-tetrahydrofuranyl 4.9 I Cl O3-tetrahydrofuranyl 4.10 Me SO₂Me O 3-tetrahydrofuranyl oil, Rf = 0.1(EA) 4.11 Me SO₂Et O 3-tetrahydrofuranyl 4.12 Me Cl O3-tetrahydrofuranyl 4.13 SMe SO₂Me O 3-tetrahydrofuranyl 4.14 SMe SO₂EtO 3-tetrahydrofuranyl 4.15 SMe Cl O 3-tetrahydrofuranyl 4.16 SO₂Me SO₂MeO 3-tetrahydrofuranyl 4.17 SO₂Me SO₂Et O 3-tetrahydrofuranyl 4.18 SO₂MeCl O 3-tetrahydrofuranyl 4.19 NO₂ SO₂Me O 3-tetrahydrofuranyl 4.20 NO₂SO₂Et O 3-tetrahydrofuranyl 4.21 NO₂ Cl O 3-tetrahydrofuranyl 4.22 ClSO₂Me O 4-tetrahydropyranyl 4.23 Cl SO₂Et O 4-tetrahydropyranyl 4.24 ClCl O 4-tetrahydropyranyl 4.25 Br SO₂Me O 4-tetrahydropyranyl 4.26 BrSO₂Et O 4-tetrahydropyranyl 4.27 Br Cl O 4-tetrahydropyranyl 4.28 ISO₂Me O 4-tetrahydropyranyl 4.29 I SO₂Et O 4-tetrahydropyranyl 4.30 I ClO 4-tetrahydropyranyl 4.31 Me SO₂Me O 4-tetrahydropyranyl 4.32 Me SO₂EtO 4-tetrahydropyranyl 4.33 Me Cl O 4-tetrahydropyranyl 4.34 SMe SO₂Me O4-tetrahydropyranyl 4.35 SMe SO₂Et O 4-tetrahydropyranyl 4.36 SMe Cl O4-tetrahydropyranyl 4.37 SO₂Me SO₂Me O 4-tetrahydropyranyl 4.38 SO₂MeSO₂Et O 4-tetrahydropyranyl 4.39 SO₂Me Cl O 4-tetrahydropyranyl 4.40 NO₂SO₂Me O 4-tetrahydropyranyl 4.41 NO₂ SO₂Et O 4-tetrahydropyranyl 4.42NO₂ Cl O 4-tetrahydropyranyl 4.43 Cl SO₂Me O 3-tetrahydropyranyl 4.44 ClSO₂Et O 3-tetrahydropyranyl 4.45 Cl Cl O 3-tetrahydropyranyl 4.46 BrSO₂Me O 3-tetrahydropyranyl 4.47 Br SO₂Et O 3-tetrahydropyranyl 4.48 BrCl O 3-tetrahydropyranyl 4.49 I SO₂Me O 3-tetrahydropyranyl 4.50 I SO₂EtO 3-tetrahydropyranyl 4.51 I Cl O 3-tetrahydropyranyl 4.52 Me SO₂Me O3-tetrahydropyranyl 4.53 Me SO₂Et O 3-tetrahydropyranyl 4.54 Me Cl O3-tetrahydropyranyl 4.55 SMe SO₂Me O 3-tetrahydropyranyl 4.56 SMe SO₂EtO 3-tetrahydropyranyl 4.57 SMe Cl O 3-tetrahydropyranyl 4.58 SO₂Me SO₂MeO 3-tetrahydropyranyl 4.59 SO₂Me SO₂Et O 3-tetrahydropyranyl 4.60 SO₂MeCl O 3-tetrahydropyranyl 4.61 NO₂ SO₂Me O 3-tetrahydropyranyl 4.62 NO₂SO₂Et O 3-tetrahydropyranyl 4.63 NO₂ Cl O 3-tetrahydropyranyl 4.64 ClSO₂Me O 1,3-dioxan-5-yl 4.65 Cl SO₂Et O 1,3-dioxan-5-yl 4.66 Cl Cl O1,3-dioxan-5-yl 4.67 Br SO₂Me O 1,3-dioxan-5-yl 4.68 Br SO₂Et O1,3-dioxan-5-yl 4.69 Br Cl O 1,3-dioxan-5-yl 4.70 I SO₂Me O1,3-dioxan-5-yl 4.71 I SO₂Et O 1,3-dioxan-5-yl 4.72 I Cl O1,3-dioxan-5-yl 4.73 Me SO₂Me O 1,3-dioxan-5-yl 4.74 Me SO₂Et O1,3-dioxan-5-yl 4.75 Me Cl O 1,3-dioxan-5-yl 4.76 SMe SO₂Me O1,3-dioxan-5-yl 4.77 SMe SO₂Et O 1,3-dioxan-5-yl 4.78 SMe Cl O1,3-dioxan-5-yl 4.79 SO₂Me SO₂Me O 1,3-dioxan-5-yl 4.80 SO₂Me SO₂Et O1,3-dioxan-5-yl 4.81 SO₂Me Cl O 1,3-dioxan-5-yl 4.82 NO₂ SO₂Me O1,3-dioxan-5-yl 4.83 NO₂ SO₂Et O 1,3-dioxan-5-yl 4.84 NO₂ Cl O1,3-dioxan-5-yl 4.85 Cl SO₂Me O γ-butyrolacton-2-yl 4.86 Cl SO₂Et Oγ-butyrolacton-2-yl 4.87 Cl Cl O γ-butyrolacton-2-yl 4.88 Br SO₂Me Oγ-butyrolacton-2-yl 4.89 Br SO₂Et O γ-butyrolacton-2-yl 4.90 Br Cl Oγ-butyrolacton-2-yl 4.91 I SO₂Me O γ-butyrolacton-2-yl 4.92 I SO₂Et Oγ-butyrolacton-2-yl 4.93 I Cl O γ-butyrolacton-2-yl 4.94 Me SO₂Me Oγ-butyrolacton-2-yl 4.95 Me SO₂Et O γ-butyrolacton-2-yl 4.96 Me Cl Oγ-butyrolacton-2-yl 4.97 SMe SO₂Me O γ-butyrolacton-2-yl 4.98 SMe SO₂EtO γ-butyrolacton-2-yl 4.99 SMe Cl O γ-butyrolacton-2-yl 4.100 SO₂MeSO₂Me O γ-butyrolacton-2-yl 4.101 SO₂Me SO₂Et O γ-butyrolacton-2-yl4.102 SO₂Me Cl O γ-butyrolacton-2-yl 4.103 NO₂ SO₂Me Oγ-butyrolacton-2-yl 4.104 NO₂ SO₂Et O γ-butyrolacton-2-yl 4.105 NO₂ Cl Oγ-butyrolacton-2-yl 4.106 Cl SO₂Me S 3-tetrahydrofuranyl 4.107 Cl SO₂EtS 3-tetrahydrofuranyl 4.108 Cl Cl S 3-tetrahydrofuranyl 4.109 Br SO₂Me S3-tetrahydrofuranyl 4.110 Br SO₂Et S 3-tetrahydrofuranyl 4.111 Br Cl S3-tetrahydrofuranyl 4.112 I SO₂Me S 3-tetrahydrofuranyl 4.113 I SO₂Et S3-tetrahydrofuranyl 4.114 I Cl S 3-tetrahydrofuranyl 4.115 Me SO₂Me S3-tetrahydrofuranyl 4.116 Me SO₂Et S 3-tetrahydrofuranyl 4.117 Me Cl S3-tetrahydrofuranyl 4.118 SMe SO₂Me S 3-tetrahydrofuranyl 4.119 SMeSO₂Et S 3-tetrahydrofuranyl 4.120 SMe Cl S 3-tetrahydrofuranyl 4.121SO₂Me SO₂Me S 3-tetrahydrofuranyl 4.122 SO₂Me SO₂Et S3-tetrahydrofuranyl 4.123 SO₂Me Cl S 3-tetrahydrofuranyl 4.124 NO₂ SO₂MeS 3-tetrahydrofuranyl 4.125 NO₂ SO₂Et S 3-tetrahydrofuranyl 4.126 NO₂ ClS 3-tetrahydrofuranyl 4.127 Cl SO₂Me S 4-tetrahydropyranyl 4.128 ClSO₂Et S 4-tetrahydropyranyl 4.129 Cl Cl S 4-tetrahydropyranyl 4.130 BrSO₂Me S 4-tetrahydropyranyl 4.131 Br SO₂Et S 4-tetrahydropyranyl 4.132Br Cl S 4-tetrahydropyranyl 4.133 I SO₂Me S 4-tetrahydropyranyl 4.134 ISO₂Et S 4-tetrahydropyranyl 4.135 I Cl S 4-tetrahydropyranyl 4.136 MeSO₂Me S 4-tetrahydropyranyl 4.137 Me SO₂Et S 4-tetrahydropyranyl 4.138Me Cl S 4-tetrahydropyranyl 4.139 SMe SO₂Me S 4-tetrahydropyranyl 4.140SMe SO₂Et S 4-tetrahydropyranyl 4.141 SMe Cl S 4-tetrahydropyranyl 4.142SO₂Me SO₂Me S 4-tetrahydropyranyl 4.143 SO₂Me SO₂Et S4-tetrahydropyranyl 4.144 SO₂Me Cl S 4-tetrahydropyranyl 4.145 NO₂ SO₂MeS 4-tetrahydropyranyl 4.146 NO₂ SO₂Et S 4-tetrahydropyranyl 4.147 NO₂ ClS 4-tetrahydropyranyl 4.148 Cl SO₂Me S 3-tetrahydropyranyl 4.149 ClSO₂Et S 3-tetrahydropyranyl 4.150 Cl Cl S 3-tetrahydropyranyl 4.151 BrSO₂Me S 3-tetrahydropyranyl 4.152 Br SO₂Et S 3-tetrahydropyranyl 4.153Br Cl S 3-tetrahydropyranyl 4.154 I SO₂Me S 3-tetrahydropyranyl 4.155 ISO₂Et S 3-tetrahydropyranyl 4.156 I Cl S 3-tetrahydropyranyl 4.157 MeSO₂Me S 3-tetrahydropyranyl 4.158 Me SO₂Et S 3-tetrahydropyranyl 4.159Me Cl S 3-tetrahydropyranyl 4.160 SMe SO₂Me S 3-tetrahydropyranyl 4.161SMe SO₂Et S 3-tetrahydropyranyl 4.162 SMe Cl S 3-tetrahydropyranyl 4.163SO₂Me SO₂Me S 3-tetrahydropyranyl 4.164 SO₂Me SO₂Et S3-tetrahydropyranyl 4.165 SO₂Me Cl S 3-tetrahydropyranyl 4.166 NO₂ SO₂MeS 3-tetrahydropyranyl 4.167 NO₂ SO₂Et S 3-tetrahydropyranyl 4.168 NO₂ ClS 3-tetrahydropyranyl 4.169 Cl SO₂Me S 1,3-dioxan-5-yl 4.170 Cl SO₂Et S1,3-dioxan-5-yl 4.171 Cl Cl S 1,3-dioxan-5-yl 4.172 Br SO₂Me S1,3-dioxan-5-yl 4.173 Br SO₂Et S 1,3-dioxan-5-yl 4.174 Br Cl S1,3-dioxan-5-yl 4.175 I SO₂Me S 1,3-dioxan-5-yl 4.176 I SO₂Et S1,3-dioxan-5-yl 4.177 I Cl S 1,3-dioxan-5-yl 4.178 Me SO₂Me S1,3-dioxan-5-yl 4.179 Me SO₂Et S 1,3-dioxan-5-yl 4.180 Me Cl S1,3-dioxan-5-yl 4.181 SMe SO₂Me S 1,3-dioxan-5-yl 4.182 SMe SO₂Et S1,3-dioxan-5-yl 4.183 SMe Cl S 1,3-dioxan-5-yl 4.184 SO₂Me SO₂Me S1,3-dioxan-5-yl 4.185 SO₂Me SO₂Et S 1,3-dioxan-5-yl 4.186 SO₂Me Cl S1,3-dioxan-5-yl 4.187 NO₂ SO₂Me S 1,3-dioxan-5-yl 4.188 NO₂ SO₂Et S1,3-dioxan-5-yl 4.189 NO₂ Cl S 1,3-dioxan-5-yl 4.190 Cl SO₂Me Sγ-butyrolacton-2-yl 4.191 Cl SO₂Et S γ-butyrolacton-2-yl 4.192 Cl Cl Sγ-butyrolacton-2-yl 4.193 Br SO₂Me S γ-butyrolacton-2-yl 4.194 Br SO₂EtS γ-butyrolacton-2-yl 4.195 Br Cl S γ-butyrolacton-2-yl 4.196 I SO₂Me Sγ-butyrolacton-2-yl 4.197 I SO₂Et S γ-butyrolacton-2-yl 4.198 I Cl Sγ-butyrolacton-2-yl 4.199 Me SO₂Me S γ-butyrolacton-2-yl 4.200 Me SO₂EtS γ-butyrolacton-2-yl 4.201 Me Cl S γ-butyrolacton-2-yl 4.202 SMe SO₂MeS γ-butyrolacton-2-yl 4.203 SMe SO₂Et S γ-butyrolacton-2-yl 4.204 SMe ClS γ-butyrolacton-2-yl 4.205 SO₂Me SO₂Me S γ-butyrolacton-2-yl 4.206SO₂Me SO₂Et S γ-butyrolacton-2-yl 4.207 SO₂Me Cl S γ-butyrolacton-2-yl4.208 NO₂ SO₂Me S γ-butyrolacton-2-yl 4.209 NO₂ SO₂Et Sγ-butyrolacton-2-yl 4.210 NO₂ Cl S γ-butyrolacton-2-yl

TABLE 5 Compounds of the formula (l) according to the invention in whichthe substituents and symbols are as defined below: R³ = H Q = Q2 R⁶ = HR⁷ = Me R⁸ = H

No. R¹ R² X Het Physical data 5.1 Cl SO₂Me O 3-tetrahydrofuranyl oil, Rf= 0.1 (EA) 5.2 Cl SO₂Et O 3-tetrahydrofuranyl oil, Rf = 0.1 (EA) 5.3 ClCl O 3-tetrahydrofuranyl 5.4 Br SO₂Me O 3-tetrahydrofuranyl 5.5 Br SO₂EtO 3-tetrahydrofuranyl 5.6 Br Cl O 3-tetrahydrofuranyl 5.7 l SO₂Me O3-tetrahydrofuranyl 5.8 l SO₂Et O 3-tetrahydrofuranyl 5.9 l Cl O3-tetrahydrofuranyl 5.10 Me SO₂Me O 3-tetrahydrofuranyl 5.11 Me SO₂Et O3-tetrahydrofuranyl 5.12 Me Cl O 3-tetrahydrofuranyl 5.13 SMe SO₂Me O3-tetrahydrofuranyl 5.14 SMe SO₂Et O 3-tetrahydrofuranyl 5.15 SMe Cl O3-tetrahydrofuranyl 5.16 SO₂Me SO₂Me O 3-tetrahydrofuranyl 5.17 SO₂MeSO₂Et O 3-tetrahydrofuranyl 5.18 SO₂Me Cl O 3-tetrahydrofuranyl 5.19 NO₂SO₂Me O 3-tetrahydrofuranyl 5.20 NO₂ SO₂Et O 3-tetrahydrofuranyl 5.21NO₂ Cl O 3-tetrahydrofuranyl 5.22 Cl SO₂Me O 4-tetrahydropyranyl 5.23 ClSO₂Et O 4-tetrahydropyranyl 5.24 Cl Cl O 4-tetrahydropyranyl 5.25 BrSO₂Me O 4-tetrahydropyranyl 5.26 Br SO₂Et O 4-tetrahydropyranyl 5.27 BrCl O 4-tetrahydropyranyl 5.28 l SO₂Me O 4-tetrahydropyranyl 5.29 l SO₂EtO 4-tetrahydropyranyl 5.30 l Cl O 4-tetrahydropyranyl 5.31 Me SO₂Me O4-tetrahydropyranyl 5.32 Me SO₂Et O 4-tetrahydropyranyl 5.33 Me Cl O4-tetrahydropyranyl 5.34 SMe SO₂Me O 4-tetrahydropyranyl 5.35 SMe SO₂EtO 4-tetrahydropyranyl 5.36 SMe Cl O 4-tetrahydropyranyl 5.37 SO₂Me SO₂MeO 4-tetrahydropyranyl 5.38 SO₂Me SO₂Et O 4-tetrahydropyranyl 5.39 SO₂MeCl O 4-tetrahydropyranyl 5.40 NO₂ SO₂Me O 4-tetrahydropyranyl 5.41 NO₂SO₂Et O 4-tetrahydropyranyl 5.42 NO₂ Cl O 4-tetrahydropyranyl 5.43 ClSO₂Me O 3-tetrahydropyranyl 5.44 Cl SO₂Et O 3-tetrahydropyranyl 5.45 ClCl O 3-tetrahydropyranyl 5.46 Br SO₂Me O 3-tetrahydropyranyl 5.47 BrSO₂Et O 3-tetrahydropyranyl 5.48 Br Cl O 3-tetrahydropyranyl 5.49 lSO₂Me O 3-tetrahydropyranyl 5.50 l SO₂Et O 3-tetrahydropyranyl 5.51 l ClO 3-tetrahydropyranyl 5.52 Me SO₂Me O 3-tetrahydropyranyl 5.53 Me SO₂EtO 3-tetrahydropyranyl 5.54 Me Cl O 3-tetrahydropyranyl 5.55 SMe SO₂Me O3-tetrahydropyranyl 5.56 SMe SO_(2Et) O 3-tetrahydropyranyl 5.57 SMe ClO 3-tetrahydropyranyl 5.58 SO₂Me SO₂Me O 3-tetrahydropyranyl 5.59 SO₂MeSO₂Et O 3-tetrahydropyranyl 5.60 SO₂Me Cl O 3-tetrahydropyranyl 5.61 NO₂SO₂Me O 3-tetrahydropyranyl 5.62 NO₂ SO₂Et O 3-tetrahydropyranyl 5.63NO₂ Cl O 3-tetrahydropyranyl 5.64 Cl SO₂Me O 1,3-dioxan-5-yl 5.65 ClSO₂Et O 1,3-dioxan-5-yl 5.66 Cl Cl O 1,3-dioxan-5-yl 5.67 Br SO₂Me O1,3-dioxan-5-yl 5.68 Br SO₂Et O 1,3-dioxan-5-yl 5.69 Br Cl O1,3-dioxan-5-yl 5.70 l SO₂Me O 1,3-dioxan-5-yl 5.71 l SO₂Et O1,3-dioxan-5-yl 5.72 l Cl O 1,3-dioxan-5-yl 5.73 Me SO₂Me O1,3-dioxan-5-yl 5.74 Me SO₂Et O 1,3-dioxan-5-yl 5.75 Me Cl O1,3-dioxan-5-yl 5.76 SMe SO₂Me O 1,3-dioxan-5-yl 5.77 SMe SO₂Et O1,3-dioxan-5-yl 5.78 SMe Cl O 1,3-dioxan-5-yl 5.79 SO₂Me SO₂Me O1,3-dioxan-5-yl 5.80 SO₂Me SO₂Et O 1,3-dioxan-5-yl 5.81 SO₂Me Cl O1,3-dioxan-5-yl 5.82 NO₂ SO₂Me O 1,3-dioxan-5-yl 5.83 NO₂ SO₂Et O1,3-dioxan-5-yl 5.84 NO₂ Cl O 1,3-dioxan-5-yl 5.85 Cl SO₂Me Oγ-butyrolacton-2-yl 5.86 Cl SO₂Et O γ-butyrolacton-2-yl 5.87 Cl Cl Oγ-butyrolacton-2-yl 5.88 Br SO₂Me O γ-butyrolacton-2-yl 5.89 Br SO₂Et Oγ-butyrolacton-2-yl 5.90 Br Cl O γ-butyrolacton-2-yl 5.91 l SO₂Me Oγ-butyrolacton-2-yl 5.92 l SO₂Et O γ-butyrolacton-2-yl 5.93 l Cl Oγ-butyrolacton-2-yl 5.94 Me SO₂Me O γ-butyrolacton-2-yl 5.95 Me SO₂Et Oγ-butyrolacton-2-yl 5.96 Me Cl O γ-butyrolacton-2-yl 5.97 SMe SO₂Me Oγ-butyrolacton-2-yl 5.98 SMe SO₂Et O γ-butyrolacton-2-yl 5.99 SMe Cl Oγ-butyrolacton-2-yl 5.100 SO₂Me SO₂Me O γ-butyrolacton-2-yl 5.101 SO₂MeSO₂Et O γ-butyrolacton-2-yl 5.102 SO₂Me Cl O γ-butyrolacton-2-yl 5.103NO₂ SO₂Me O γ-butyrolacton-2-yl 5.104 NO₂ SO₂Et O γ-butyrolacton-2-yl5.105 NO₂ Cl O γ-butyrolacton-2-yl 5.106 Cl SO₂Me S 3-tetrahydrofuranyl5.107 Cl SO₂Et S 3-tetrahydrofuranyl 5.108 Cl Cl S 3-tetrahydrofuranyl5.109 Br SO₂Me S 3-tetrahydrofuranyl 5.110 Br SO₂Et S3-tetrahydrofuranyl 5.111 Br Cl S 3-tetrahydrofuranyl 5.112 l SO₂Me S3-tetrahydrofuranyl 5.113 l SO₂Et S 3-tetrahydrofuranyl 5.114 l Cl S3-tetrahydrofuranyl 5.115 Me SO₂Me S 3-tetrahydrofuranyl 5.116 Me SO₂EtS 3-tetrahydrofuranyl 5.117 Me Cl S 3-tetrahydrofuranyl 5.118 SMe SO₂MeS 3-tetrahydrofuranyl 5.119 SMe SO₂Et S 3-tetrahydrofuranyl 5.120 SMe ClS 3-tetrahydrofuranyl 5.121 SO₂Me SO₂Me S 3-tetrahydrofuranyl 5.122SO₂Me SO₂Et S 3-tetrahydrofuranyl 5.123 SO₂Me Cl S 3-tetrahydrofuranyl5.124 NO₂ SO₂Me S 3-tetrahydrofuranyl 5.125 NO₂ SO₂Et S3-tetrahydrofuranyl 5.126 NO₂ Cl S 3-tetrahydrofuranyl 5.127 Cl SO₂Me S4-tetrahydropyranyl 5.128 Cl SO₂Et S 4-tetrahydropyranyl 5.129 Cl Cl S4-tetrahydropyranyl 5.130 Br SO₂Me S 4-tetrahydropyranyl 5.131 Br SO₂EtS 4-tetrahydropyranyl 5.132 Br Cl S 4-tetrahydropyranyl 5.133 l SO₂Me S4-tetrahydropyranyl 5.134 l SO₂Et S 4-tetrahydropyranyl 5.135 l Cl S4-tetrahydropyranyl 5.136 Me SO₂Me S 4-tetrahydropyranyl 5.137 Me SO₂EtS 4-tetrahydropyranyl 5.138 Me Cl S 4-tetrahydropyranyl 5.139 SMe SO₂MeS 4-tetrahydropyranyl 5.140 SMe SO₂Et S 4-tetrahydropyranyl 5.141 SMe ClS 4-tetrahydropyranyl 5.142 SO₂Me SO₂Me S 4-tetrahydropyranyl 5.143SO₂Me SO₂Et S 4-tetrahydropyranyl 5.144 SO₂Me Cl S 4-tetrahydropyranyl5.145 NO₂ SO₂Me S 4-tetrahydropyranyl 5.146 NO₂ SO₂Et S4-tetrahydropyranyl 5.147 NO₂ Cl S 4-tetrahydropyranyl 5.148 Cl SO₂Me S3-tetrahydropyranyl 5.149 Cl SO₂Et S 3-tetrahydropyranyl 5.150 Cl Cl S3-tetrahydropyranyl 5.151 Br SO₂Me S 3-tetrahydropyranyl 5.152 Br SO₂EtS 3-tetrahydropyranyl 5.153 Br Cl S 3-tetrahydropyranyl 5.154 l SO₂Me S3-tetrahydropyranyl 5.155 l SO₂Et S 3-tetrahydropyranyl 5.156 l Cl S3-tetrahydropyranyl 5.157 Me SO₂Me S 3-tetrahydropyranyl 5.158 Me SO₂EtS 3-tetrahydropyranyl 5.159 Me Cl S 3-tetrahydropyranyl 5.160 SMe SO₂MeS 3-tetrahydropyranyl 5.161 SMe SO₂Et S 3-tetrahydropyranyl 5.162 SMe ClS 3-tetrahydropyranyl 5.163 SO₂Me SO₂Me S 3-tetrahydropyranyl 5.164SO₂Me SO₂Et S 3-tetrahydropyranyl 5.165 SO₂Me Cl S 3-tetrahydropyranyl5.166 NO₂ SO₂Me S 3-tetrahydropyranyl 5.167 NO₂ SO₂Et S3-tetrahydropyranyl 5.168 NO₂ Cl S 3-tetrahydropyranyl 5.169 Cl SO₂Me S1,3-dioxan-5-yl 5.170 Cl SO₂Et S 1,3-dioxan-5-yl 5.171 Cl Cl S1,3-dioxan-5-yl 5.172 Br SO₂Me S 1,3-dioxan-5-yl 5.173 Br SO₂Et S1,3-dioxan-5-yl 5.174 Br Cl S 1,3-dioxan-5-yl 5.175 l SO₂Me S1,3-dioxan-5-yl 5.176 l SO₂Et S 1,3-dioxan-5-yl 5.177 l Cl S1,3-dioxan-5-yl 5.178 Me SO₂Me S 1,3-dioxan-5-yl 5.179 Me SO₂Et S1,3-dioxan-5-yl 5.180 Me Cl S 1,3-dioxan-5-yl 5.181 SMe SO₂Me S1,3-dioxan-5-yl 5.182 SMe SO₂Et S 1,3-dioxan-5-yl 5.183 SMe Cl S1,3-dioxan-5-yl 5.184 SO₂Me SO₂Me S 1,3-dioxan-5-yl 5.185 SO₂Me SO₂Et S1,3-dioxan-5-yl 5.186 SO₂Me Cl S 1,3-dioxan-5-yl 5.187 NO₂ SO₂Me S1,3-dioxan-5-yl 5.188 NO₂ SO₂Et S 1,3-dioxan-5-yl 5.189 NO₂ Cl S1,3-dioxan-5-yl 5.190 Cl SO₂Me S γ-butyrolacton-2-yl 5.191 Cl SO₂Et Sγ-butyrolacton-2-yl 5.192 Cl Cl S γ-butyrolacton-2-yl 5.193 Br SO₂Me Sγ-butyrolacton-2-yl 5.194 Br SO₂Et S γ-butyrolacton-2-yl 5.195 Br Cl Sγ-butyrolacton-2-yl 5.196 l SO₂Me S γ-butyrolacton-2-yl 5.197 l SO₂Et Sγ-butyrolacton-2-yl 5.198 l Cl S γ-butyrolacton-2-yl 5.199 Me SO₂Me Sγ-butyrolacton-2-yl 5.200 Me SO₂Et S γ-butyrolacton-2-yl 5.201 Me Cl Sγ-butyrolacton-2-yl 5.202 SMe SO₂Me S γ-butyrolacton-2-yl 5.203 SMeSO₂Et S γ-butyrolacton-2-yl 5.204 SMe Cl S γ-butyrolacton-2-yl 5.205SO₂Me SO₂Me S γ-butyrolacton-2-yl 5.206 SO₂Me SO₂Et Sγ-butyrolacton-2-yl 5.207 SO₂Me Cl S γ-butyrolacton-2-yl 5.208 NO₂ SO₂MeS γ-butyrolacton-2-yl 5.209 NO₂ SO₂Et S γ-butyrolacton-2-yl 5.210 NO₂ ClS γ-butyrolacton-2-yl 5.211 OMe Cl O 3-tetrahydrofuranyl oil, Rf = 0.1(EA)

TABLE 6 Compounds of the formula (l) according to the invention in whichthe substituents and symbols are as defined below: R³ = H Q = Q2 R⁶ = HR⁷ = Et R⁸ = H

No. R¹ R² X Het Physical data 6.1 Cl SO₂Me O 3 tetrahydrofuranyl oil, Rf= 0.1 (EA) 6.2 Cl SO₂Et O 3 tetrahydrofuranyl 6.3 Cl Cl O 3tetrahydrofuranyl 6.4 Br SO₂Me O 3 tetrahydrofuranyl 6.5 Br SO₂Et O3-tetrahydrofuranyl 6.6 Br Cl O 3-tetrahydrofuranyl 6.7 l SO₂Me O3-tetrahydrofuranyl 6.8 l SO₂Et O 3-tetrahydrofuranyl 6.9 cl O3-tetrahydrofuranyl 6.10 Me SO₂Me O 3-tetrahydrofuranyl 6.11 Me SO₂Et O3-tetrahydrofuranyl 6.12 Me Cl O 3-tetrahydrofuranyl 6.13 SMe SO₂Me O3-tetrahydrofuranyl 6.14 SMe SO₂Et O 3-tetrahydrofuranyl 6.15 SMe Cl O3-tetrahydrofuranyl 6.16 SO₂Me SO₂Me O 3-tetrahydrofuranyl 6.17 SO₂MeSO₂Et O 3-tetrahydrofuranyl 6.18 SO₂Me Cl O 3-tetrahydrofuranyl 6.19 NO₂SO₂Me O 3-tetrahydrofuranyl 6.20 NO₂ SO₂Et O 3-tetrahydrofuranyl 6.21NO₂ cl O 3-tetrahydrofuranyl 6.22 Cl SO₂Me O 4-tetrahydropyranyl 6.23 ClSO₂Et O 4-tetrahydropyranyl 6.24 Cl Cl O 4-tetrahydropyranyl 6.25 BrSO₂Me O 4-tetrahydropyranyl 6.26 Br SO₂Et O 4-tetrahydropyranyl 6.27 BrCl O 4-tetrahydropyranyl 6.28 l SO₂Me O 4-tetrahydropyranyl 6.29 l SO₂EtO 4-tetrahydropyranyl 6.30 l Cl O 4-tetrahydropyranyl 6.31 Me SO₂Me O4-tetrahydropyranyl 6.32 Me SO₂Et O 4-tetrahydropyranyl 6.33 Me Cl O4-tetrahydropyranyl 6.34 SMe SO₂Me O 4-tetrahydropyranyl 6.35 SMe SO₂EtO 4-tetrahydropyranyl 6.36 SMe Cl O 4-tetrahydropyranyl 6.37 SO₂Me SO₂MeO 4-tetrahydropyranyl 6.38 SO₂Me SO₂Et O 4-tetrahydropyranyl 6.39 SO₂MeCl O 4-tetrahydropyranyl 6.40 NO₂ SO₂Me O 4-tetrahydropyranyl 6.41 NO₂SO₂Et O 4-tetrahydropyranyl 6.42 NO₂ Cl O 4-tetrahydropyranyl 6.43 ClSO₂Me O 3-tetrahydropyranyl 6.44 Cl SO₂Et O 3-tetrahydropyranyl 6.45 ClCl O 3-tetrahydropyranyl 6.46 Br SO₂Me O 3-tetrahydropyranyl 6.47 BrSO₂Et O 3-tetrahydropyranyl 6.48 Br Cl O 3-tetrahydropyranyl 6.49 lSO₂Me O 3-tetrahydropyranyl 6.50 l SO₂Et O 3-tetrahydropyranyl 6.51 l ClO 3-tetrahydropyranyl 6.52 Me SO₂Me O 3-tetrahydropyfanyl 6.53 Me SO₂EtO 3-tetrahydropyranyl 6.54 Me Cl O 3-tetrahydropyranyl 6.55 SMe SO₂Me O3-tetrahydropyranyl 6.56 SMe SO₂Et O 3-tetrahydropyranyl 6.57 SMe Cl O3-tetrahydropyranyl 6.58 SO₂Me SO₂Me O 3-tetrahydropyranyl 6.59 SO₂MeSO₂Et O 3-tetrahydropyranyl 6.60 SO₂Me Cl O 3-tetrahydropyranyl 6.61 NO₂SO₂Me O 3-tetrahydropyranyl 6.62 NO₂ SO₂Et O 3-tetrahydropyranyl 6.63NO2 Cl O 3-tetrahydropyranyl 6.64 Cl SO₂Me O 1,3-dioxan-5-yl 6.65 ClSO₂Et O 1,3-dioxan-5-yl 6.66 Cl Cl O 1,3-dioxan-5-yl 6.67 Br SO₂Me O1,3-dioxan-5-yl 6.68 Br SO₂Et O 1,3-dioxan-5-yl 6.69 Br Cl O1,3-dioxan-5-yl 6.7O l SO₂Me O 1,3-dioxan-5-yl 6.71 l SO₂Et O1,3-dioxan-5-yl 6.72 l Cl O 1,3-dioxan-5-yl 6.73 Me SO₂Me O1,3-dioxan-5-yl 6.74 Me SO₂Et O 1,3-dioxan-5-yl 6.75 Me Cl O1,3-dioxan-5-yl 6.76 SMe SO₂Me O 1,3-dioxan-5-yl 6.77 SMe SO₂Et O1,3-dioxan-5-yl 6.78 SMe Cl O 1,3-dioxan-5-yl 6.79 SO₂Me SO₂Me O1,3-dioxan-5-yl 6.80 SO₂Me SO₂Et O 1,3-dioxan-5-yl 6.81 SO₂Me Cl O1,3-dioxan-5-yl 6.82 NO₂ SO₂Me O 1,3-dioxan-5-yl 6.83 NO₂ SO₂Et O1,3-dioxan-5-yl 6.84 NO₂ Cl O 1,3-dioxan-5-yl 6.85 Cl SO₂Me Oγ-butyrolacton-2-yl 6.86 Cl SO₂Et O γ-butyrolacton-2-yl 6.87 Cl Cl Oγ-butyrolacton-2-yl 6.88 Br SO₂Me O γ-butyrolacton-2-yl 6.89 Br SO₂Et Oγ-butyrolacton-2-yl 6.90 Br Cl O γ-butyrolacton-2-yl 6.91 l SO₂Me Oγ-butyrolacton-2-yl 6.92 l SO₂Et O γ-butyrolacton-2-yl 6.93 l Cl Oγ-butyrolacton-2-yl 6.94 Me SO₂Me O γ-butyrolacton-2-yl 6.95 Me SO₂Et Oγ-butyrolacton-2-y1 6.96 Me Cl O γ-butyrolacton-2-yl 6.97 SMe SO₂Me Oγ-butyrolacton-2-yl 6.98 SMe SO₂Et O γ-butyrolacton-2-yl 6.99 SMe Cl Oγ-butyrolacton-2-yl 6.100 SO₂Me SO₂Me O γ-butyrolacton-2-yl 6.101 SO₂MeSO₂Et O γ-butyrolacton-2-yl 6.102 SO₂Me Cl O γ-butyrolacton-2-yl 6.103NO₂ SO₂Me O γ-butyrolacton-2-Yl 6.104 NO₂ SO₂Et O γ-butyrolacton-2-yl6.105 NO₂ Cl O γ-butyrolacton-2-yl 6.106 Cl SO₂Me S 3-tetrahydrofuranyl6.107 Cl SO₂Et S 3-tetrahydrofuranyl 6.108 Cl Cl S 3-tetrahydrofuranyl6.109 Br SO₂Me S 3-tetrahydrofuranyl 6.110 Br SO₂Et S3-tetrahydrofuranyl 6.111 Br Cl S 3-tetrahydrofuranyl 6.112 l SO₂Me S3-tetrahydrofuranyl 6.113 l SO₂Et S 3-tetrahydrofuranyl 6.114 l Cl S3-tetrahydrofuranyl 6.115 Me SO₂Me S 3-tetrahydrofuranyl 6.116 Me SO₂EtS 3-tetrahydrofuranyl 6.117 Me Cl S 3-tetrahydrofuranyl 6.118 SMe SO₂MeS 3-tetrahydrofuranyl 6.119 SMe SO₂Et S 3-tetrahydrofuranyl 6.120 SMe ClS 3-tetrahydrofuranyl 6.121 SO₂Me SO₂Me S 3-tetrahydrofuranyl 6.122SO₂Me SO₂Et S 3-tetrahydrofuranyl 6.123 SO₂Me Cl S 3-tetrahydrofuranyl6.124 NO₂ SO₂Me S 3-tetrahydrofuranyl 6.125 NO₂ SO₂Et S3-tetrahydrofuranyl 6.126 NO₂ Cl S 3-tetrahydrofuranyl 6.127 Cl SO₂Me S4-tetrahydropyfanyl 6.128 Cl SO₂Et S 4-tetrahydropyranyl 6.129 Cl Cl S4-tetrahydropyranyl 6.130 Br SO₂Me S 4-tetrahydropyranyl 6.131 Br SO₂EtS 4-tetrahydropyranyl 6.132 Br Cl S 4-tetrahydropyranyl 6.133 l SO₂Me S4-tetrahydropyranyl 6.134 l SO₂Et S 4-tetrahydropyranyl 6.135 l Cl S4-tetrahydropyranyl 6.136 Me SO₂Me S 4-tetrahydropyranyl 6.137 Me SO₂EtS 4-tetrahydropyranyl 6.138 Me Cl S 4-tetrahydropyranyl 6.139 SMe SO₂MeS 4-tetrahydropyranyl 6.140 SMe SO₂Et S 4-tetrahydropyranyl 6.141 SMe ClS 4-tetrahydropyranyl 6.142 SO₂Me SO₂Me S 4-tetrahydropyranyl 6.143SO₂Me SO₂Et S 4-tetrahydropyranyl 6.144 SO₂Me Cl S 4-tetrahydropyranyl6.145 NO₂ SO₂Me S 4-tetrahydropyranyl 6.146 NO₂ SO₂Et S4-tetrahydropyranyl 6.147 NO₂ Cl S 4-tetrahydropyranyl 6.148 Cl SO₂Me S3-tetrahydropyranyl 6.149 Cl SO₂Et S 3-tetrahydropyranyl 6.150 Cl Cl S3-tetrahydropyranyl 6.151 Br SO₂Me S 3-tetrahydropyranyl 6.152 Br SO₂EtS 3-tetrahydropyranyl 6.153 Br Cl S 3-tetrahydropyranyl 6.154 l SO₂Me S3-tetrahydropyranyl 6.155 l SO₂Et S 3-tetrahydropyranyl 6.156 l Cl S3-tetrahydropyranyl 6.157 Me SO₂Me S 3-tetrahydropyranyl 6.158 Me SO₂EtS 3-tetrahydropyranyl 6.159 Me Cl S 3-tetrahydropyranyl 6.160 SMe SO₂MeS 3-tetrahydropyranyl 6.161 SMe SO₂Et S 3-tetrahydropyranyl 6.162 SMe ClS 3-tetrahydropyranyl 6.163 SO₂Me SO₂Me S 3-tetrahydropyranyl 6.164SO₂Me SO₂Et S 3-tetrahydropyranyl 6.165 SO₂Me Cl S 3-tetrahydropyranyl6.166 NO₂ SO₂Me S 3-tetrahydropyranyl 6.167 NO₂ SO₂Et S3-tetrahydropyranyl 6.168 NO₂ Cl S 3-tetrahydropyranyl 6.169 Cl SO₂Me St3-dioxan-5-yl 6.170 Cl SO₂Et S 1,3-dioxan-5-yl 6.171 Cl Cl S1,3-dioxan-5-yl 6.172 Br SO₂Me S 1,3-dioxan-5-yl 6.173 Br SO₂Et S1,3-dioxan-5-yl 6.174 Br Cl S 1,3-dioxan-5-yl 6.175 l SO₂Me S1,3-dioxan-5-yl 6.176 l SO₂Et S 1,3-dioxan-5-yl 6.177 l Cl S1,3-dioxan-5-yl 6.178 Me SO₂Me S 1,3-dioxan-5-yl 6.179 Me SO₂Et S1,3-dioxan-5-yl 6.180 Me Cl S 1,3-dioxan-5-yl 6.181 SMe SO₂Me S1,3-dioxan-5-yl 6.182 SMe SO₂Et S 1,3-dioxan-5-yl 6.183 SMe Cl S1,3-dioxan-5-yl 6.184 SO₂Me SO₂Me S 1,3-dioxan-5-yl 6.185 SO₂Me SO₂Et S1,3-dioxan-5-yl 6.186 SO₂Me Cl S 1,3-dioxan-5-yl 6.187 NO₂ SO₂Me S1,3-dioxan-5-yl 6.188 NO₂ SO₂Et S 1,3-dioxan-5-yl 6.189 NO₂ Cl S1,3-dioxan-5-yl 6.190 Cl SO₂Me S γ-butyrolacton-2-yl 6.191 Cl SO₂Et Sγ-butyrolacton-2-yl 6.192 Cl Cl S γ-butyrolacton-2-yl 6.193 Br SO₂Me Sγ-butyrolacton-2-yl 6.194 Br SO₂Et S γ-butyrolacton-2-yl 6.195 Br Cl Sγ-butyrolacton-2-yl 6.196 l SO₂Me S γ-butyrolacton-2-yl 6.197 l SO₂Et Sγ-butyrolacton-2-yl 6.198 l Cl S γ-butyrolacton-2-yl 6.199 Me SO₂Me Sγ-butyrolacton-2-yl 6.200 Me SO₂Et S γ-butyrolacton-2-yl 6.201 Me Cl Sγ-butyrolacton-2-yl 6.202 SMe SO₂Me S γ-butyrolacton-2-yl 6.203 SMeSO₂Et S γ-butyrolacton-2-yl 6.204 SMe Cl S γ-butyrolacton-2-yl 6.205SO₂Me SO₂Me S γ-butyrolacton-2-yl 6.206 SO₂Me SO₂Et Sγ-butyrolacton-2-yl 6.207 SO₂Me Cl S γ-butyrolacton-2-yl 6.208 NO₂ SO₂MeS γ-butyrolacton-2-yl 6.209 NO₂ SO₂Et S γ-butyrolacton-2-yl 6.210 NO₂ ClS γ-butyrolacton-2-yl

TABLE 7 Compounds of the formula (l) according to the invention in whichthe substituents and symbols are as defined below: R³ = H Q = Q2 R⁷ = MeR⁸ = H R⁶ = cyclopropyl

No. R¹ R² X Het Physical data 7.1 Cl SO₂Me O 3-tetrahydrofuranyl 7.2 ClSO₂Et O 3-tetrahydrofuranyl 7.3 Cl Cl O 3-tetrahydrofuranyl 7.4 Br SO₂MeO 3-tetrahydrofuranyl 7.5 Br SO₂Et O 3-tetrahydrofuranyl 7.6 Br Cl O3-tetrahydrofuranyl 7.7 l SO₂Me O 3-tetrahydrofuranyl 7.8 l SO₂Et O3-tetrahydrofuranyl 7.9 l Cl O 3-tetrahydrofuranyl 7.10 Me SO₂Me O3-tetrahydrofuranyl 7.11 Me SO₂Et O 3-tetrahydrofuranyl 7.12 Me Cl O3-tetrahydrofuranyl 7.13 SMe SO₂Me O 3-tetrahydrofuranyl 7.14 SMe SO₂EtO 3-tetrahydrofuranyl 7.15 SMe Cl O 3-tetrahydrofuranyl 7.16 SO₂Me SO₂MeO 3-tetrahydrofuranyl 7.17 SO₂Me SO₂Et O 3-tetrahydrofUranyl 7.18 SO₂MeCl O 3-tetrahydrofuranyl 7.19 NO₂ SO₂Me O 3-tetrahydrofuranyl 7.20 NO₂SO₂Et O 3-tetrahydrofuranyl 7.21 NO₂ Cl O 3-tetrahydrofuranyl 7.22 ClSO₂Me O 4-tetrahydropyranyl 7.23 Cl SO₂Et O 4-tetrahydropyranyl 7 24 ClCl O 4-tetrahydropyranyl 7.25 Br SO₂Me O 4-tetrahydropyranyl 7.26 BrSO₂Et O 4-tetrahydropyranyl 7.27 Br Cl O 4-tetrahydropyranyl 7.28 lSO₂Me O 4-tetrahydropyranyl 7.29 l SO₂Et O 4-tetrahydropyranyl 7.30 l ClO 4-tetrahydropyranyl 7.31 Me SO₂Me O 4-tetrahydropyranyl 7.32 Me SO₂EtO 4-tetrahydropyranyl 7.33 Me Cl O 4-tetrahydropyranyl 7.34 SMe SO₂Me O4-tetrahydropyranyl 7.35 SMe SO₂Et O 4-tetrahydropyranyl 7.36 SMe Cl O4-tetrahydropyranyl 7.37 SO₂Me SO₂Me O 4-tetrahydropyranyl 7.38 SO₂MeSO₂Et O 4-tetrahydropyranyl 7.39 SO₂Me Cl O 4-tetrahydropyranyl 7.40 NO₂SO₂Me O 4-tetrahydropyranyl 7.41 NO₂ SO₂Et O 4-tetrahydropyranyl 7.42NO₂ Cl O 4-tetrahydropyranyl 7.43 Cl SO₂Me O 3-tetrahydropyranyl 7.44 ClSO₂Et O 3-tetrahydropyranyl 7.45 Cl Cl O 3-tetrahydropyranyl 7.46 BrSO₂Me O 3-tetrahydropyranyl 7.47 Br SO₂Et O 3-tetrahydropyranyl 7.48 BrCl O 3-tetrahydropyranyl 7.49 l SO₂Me O 3-tetrahydropyranyl 7.50 l SO₂EtO 3-tetrahydropyranyl 7.51 l Cl O 3-tetrahydropyranyl 7.52 Me SO₂Me O3-tetrahydropyranyl 7.53 Me SO₂Et O 3-tetrahydropyranyl 7.54 Me Cl O3-tetrahydropyranyl 7.55 SMe SO₂Me O 3-tetrahydropyranyl 7.56 SMe SO₂EtO 3-tetrahydropyranyl 7.57 SMe Cl O 3-tetrahydropyranyl 7.58 SO₂Me SO₂MeO 3-tetrahydropyranyl 7.59 SO₂Me SO₂Et O 3-tetrahydropyranyl 7.60 SO₂MeCl O 3-tetrahydropyranyl 7.61 NO₂ SO₂Me O 3-tetrahydropyranyl 7.62 NO₂SO₂Et O 3-tetrahydropyranyl 7.63 NO₂ Cl O 3-tetrahydropyranyl 7.64 ClSO₂Me O 1,3-dioxan-5-yl 7.65 Cl SO₂Et O 1,3-dioxan-5-yl 7.66 Cl Cl O1,3-dioxan-5-yl 7.67 Br SO₂Me O 1,3-dioxan-5-yl 7.68 Br SO₂Et O1,3-dioxan-5-yl 7.69 Br Cl O 1,3-dioxan-5-yl 7.70 l SO₂Me O1,3-dioxan-5-yl 7.71 l SO₂Et O 1,3-dioxan-5-yl 7.72 l Cl O1,3-dioxan-5-yl 7.73 Me SO₂Me O 1,3-dioxan-5-yl 7.74 Me SO₂Et O1,3-dioxan-5-yl 7.75 Me Cl O 1,3-dioxan-5-yl 7.76 SMe SO₂Me O1,3-dioxan-5-yl 7.77 SMe SO₂Et O 1,3-dioxan-5-yl 7.78 SMe Cl O1,3-dioxan-5-yl 7.79 SO₂Me SO₂Me O 1,3-dioxan-5-yl 7.80 SO₂Me SO₂Et O1,3-dioxan-5-yl 7.81 SO₂Me Cl O 1,3-dioxan-5-yl 7.82 NO₂ SO₂Me O1,3-dioxan-5-yl 7.83 NO₂ SO₂Et O 1,3-dioxan-5-yl 7.84 NO₂ Cl O1,3-dioxan-5-yl 7.85 Cl SO₂Me O γ-butyrolacton-2-yl 7.86 Cl SO₂Et Oγ-butyrolacton-2-yl 7.87 Cl Cl O γ-butyrolacton-2-yl 7.88 Br SO₂Me Oγ-butyrolacton-2-yl 7.89 Br SO₂Et O γ-butyrolacton-2-yl 7.90 Br Cl Oγ-butyrolacton-2-yl 7.91 l SO₂Me O γ-butyrolacton-2-yl 7.92 l SO₂Et Oγ-butyrolacton-2-yl 7.93 l Cl O γ-butyrolacton-2-yl 7.94 Me SO₂Me Oγ-butyrolacton-2-yl 7.95 Me SO₂Et O γ-butyrolacton-2-yl 7.96 Me Cl Oγ-butyrolacton-2-yl 7.97 SMe SO₂Me O γ-butyrolacton-2-yl 7.98 SMe SO₂EtO γ-butyrolacton-2-yl 7.99 SMe Cl O γ-butyrolacton-2-yl 7.100 SO₂MeSO₂Me O γ-butyrolacton-2-yl 7.101 SO₂Me SO₂Et O γ-butyrolacton-2-yl7.102 SO₂Me Cl O γ-butyrolacton-2-Yl 7.103 NO₂ SO₂Me Oγ-butyrolacton-2-yl 7.104 NO₂ SO₂Et O γ-butyrolacton-2-Yl 7.105 NO₂ Cl Oγ-butyrolacton-2-yl 7.106 Cl SO₂Me S 3-tetrahydrofuranyl 7.107 Cl SO₂EtS 3-tetrahydrofuranyl 7.108 Cl Cl S 3-tetrahydrofuranyl 7.109 Br SO₂Me S3-tetrahydrofuranyl 7.110 Br SO₂Et S 3-tetrahydrofuranyl 7.111 Br Cl S3-tetrahydrofuranyl 7.112 l SO₂Me S 3-tetrahydrofuranyl 7.113 l SO₂Et S3-tetrahydrofuranyl 7.114 l Cl S 3-tetrahydrofuranyl 7.115 Me SO₂Me S3-tetrahydrofuranyl 7.116 Me SO₂Et S 3-tetrahydrofuranyl 7.117 Me Cl S3-tetrahydrofuranyl 7.118 SMe SO₂Me S 3-tetrahydrofuranyl 7.119 SMeSO₂Et S 3-tetrahydrofuranyl 7.120 SMe Cl S 3-tetrahydrofuranyl 7.121SO₂Me SO₂Me S 3-tetrahydrofuranyl 7.122 SO₂Me SO₂Et S3-tetrahydrofuranyl 7.123 SO₂Me Cl S 3-tetrahydrofuranyl 7.124 NO₂ SO₂MeS 3-tetrahydrofuranyl 7.125 NO₂ SO₂Et S 3-tetrahydrofuranyl 7.126 NO₂ ClS 3-tetrahydrofuranyl 7.127 Cl SO₂Me S 4-tetrahydropyranyl 7.128 ClSO₂Et S 4-tetrahydropyranyl 7.129 Cl Cl S 4-tetrahydropyranyl 7.130 BrSO₂Me S 4-tetrahydropyranyl 7.131 Br SO₂Et S 4-tetrahydropyranyl 7.132Br Cl S 4-tetrahydropyranyl 7.133 l SO₂Me S 4-tetrahydropyranyl 7.134 lSO₂Et S 4-tetrahydropyranyl 7.135 l Cl S 4-tetrahydropyranyl 7.136 MeSO₂Me S 4-tetrahydropyranyl 7.137 Me SO₂Et S 4-tetrahydropyranyl 7.138Me Cl S 4-tetrahydropyranyl 7.139 SMe SO₂Me S 4-tetrahydropyranyl 7.140SMe SO₂Et S 4-tetrahydropyranyl 7.141 SMe Cl S 4-tetrahydropyranyl 7.142SO₂Me SO₂Me S 4-tetrahydropyranyl 7.143 SO₂Me SO₂Et S4-tetrahydropyranyl 7.144 SO₂Me Cl S 4-tetrahydropyranyl 7.145 NO₂ SO₂MeS 4-tetrahydropyranyl 7.146 NO₂ SO₂Et S 4-tetrahydropyranyl 7.147 NO₂ ClS 4-tetrahydropyranyl 7.148 Cl SO₂Me S 3-tetrahydropyranyl 7.149 ClSO₂Et S 3-tetrahydropyranyl 7.150 Cl Cl S 3-tetrahydropyranyl 7.151 BrSO₂Me S 3-tetrahydropyranyl 7.152 Br SO₂Et S 3-tetrahydropyranyl 7.153Br Cl S 3-tetrahydropyranyl 7.154 l SO₂Me S 3-tetrahydropyranyl 7.155 lSO₂Et S 3-tetrahydropyranyl 7.156 l Cl S 3-tetrahydropyranyl 7.157 MeSO₂Me S 3-tetrahydropyranyl 7.158 Me SO₂Et S 3-tetrahydropyranyl 7.159Me Cl S 3-tetrahydropyranyl 7.160 SMe SO₂Me S 3-tetrahydropyranyl 7.161SMe SO₂Et S 3-tetrahydropyranyl 7.162 SMe Cl S 3-tetrahydropyranyl 7.163SO₂Me SO₂Me S 3-tetrahydropyranyl 7.164 SO₂Me SO₂Et S3-tetrahydropyranyl 7.165 SO₂Me Cl S 3-tetrahydropyranyl 7.166 NO₂ SO₂MeS 3-tetrahydropyranyl 7.167 NO₂ SO₂Et S 3-tetrahydropyranyl 7.168 NO₂ ClS 3-tetrahydropyranyl 7.169 Cl SO₂Me S 1,3-dioxan-5-yl 7.170 Cl SO₂Et S1,3-dioxan-5-yl 7.171 Cl Cl S 1,3-dioxan-5-yl 7.172 Br SO₂Me S1,3-dioxan-5-yl 7.173 Br SO₂Et S 1,3-dioxan-5-yl 7.174 Br Cl S1,3-dioxan-5-yl 7.175 l SO₂Me S 1,3-dioxan-5-yl 7.176 l SO₂Et S1,3-dioxan-5-yl 7.177 l Cl S 1,3-dioxan-5-yl 7.178 Me SO₂Me S1,3-dioxan-5-yl 7.179 Me SO₂Et S 1,3-dioxan-5-yl 7.180 Me Cl S1,3-dioxan-5-yl 7.181 SMe SO₂Me S 1,3-dioxan-5-yl 7.182 SMe SO₂Et S1,3-dioxan-5-yl 7.183 SMe Cl S 1,3-dioxan-5-yl 7.184 SO₂Me SO₂Me S1,3-dioxan-5-yl 7.185 SO₂Me SO₂Et S 1,3-dioxan-5-yl 7.186 SO₂Me Cl S1,3-dioxan-5-yl 7.187 NO₂ SO₂Me S 1,3-dioxan-5-yl 7.188 NO₂ SO₂Et S1,3-d,oxan-5-yl 7.189 NO₂ Cl S 1,3-dioxan-5-yl 7.190 Cl SO₂Me Sγ-butyrolacton-2-yl 7.191 Cl SO₂Et S γ-butyrolacton-2-yl 7.192 Cl Cl Sγ-butyrolacton-2-yl 7.193 Br SO₂Me S γ-butyrolacton-2-yl 7.194 Br SO₂EtS γ-butyrolacton-2-yl 7.195 Br Cl S γ-butyrolacton-2-yl 7.196 l SO₂Me Sγ-butyrolacton-2-yl 7.197 l SO₂Et S γ-butyrolacton-2-yl 7.198 l Cl Sγ-butyrolacton-2-yl 7.199 Me SO₂Me S γ-butyrolacton-2-yl 7.200 Me SO₂EtS γ-butyrolacton-2-yl 7.201 Me Cl S γ-butyrolacton-2-yl 7.202 SMe SO₂MeS γ-butyrolacton-2-yl 7.203 SMe SO₂Et S γ-butyrolacton-2-yl 7.204 SMe ClS γ-butyrolacton-2-yl 7.205 SO₂Me SO₂Me S γ-butyrolacton-2-yl 7.206SO₂Me SO₂Et S γ-butyrolacton-2-yl 7.207 SO₂Me Cl S γ-butyrolacton-2-yl7.208 NO₂ SO₂Me S γ-butyrolacton-2-yl 7.209 NO₂ SO₂Et Sγ-butyrolacton-2-yl 7.210 NO₂ Cl S γ-butyrolacton-2-yl

TABLE 8 Compounds of the formula (l) according to the invention in whichthe substituents and symbols are as defined below: R¹ = Cl R₂ = SO₂Me R³= H Q = Q2 X = O

No. R⁶ R⁷ R⁸ Het Physical data 8.1 H Me SOMe 3-tetrahydrofuranyl 8.2 HMe SOMe 3-tetrahydrofuranyl 8.3 H Me SO₂-nPr 3-tetrahydrofuranyl 8.4 HMe SO₂-nBu 3-tetrahydrofuranyl 8.5 H Me SO₂Ph 3-tetrahydrofuranyl 8.6 HMe CO₂Me 3-tetrahydrofuranyl 8.7 H Me CO₂Et 3-tetrahydrofuranyl 8.8 H MeCO₂-nPr 3-tetrahydrofuranyl 8.9 H Me CO₂nBu 3-tetrahydrofuranyl 8.10 HMe CO₂Ph 3-tetrahydrofuranyl 8.11 H Me Me 3-tetrahydrofuranyl 8.12 H MeEt 3-tetrahydrofuranyl 8.13 H Me nPr 3-tetrahydrofuranyl 8.14 H Me nBu3-tetrahydrofuranyl 8.15 Me Me SOMe 3-tetrahydrofuranyl 8.16 Me Me SOMe3-tetrahydrofuranyl 8.17 Me Me SO₂-nPr 3-tetrahydrofuranyl 8.18 Me MeSO₂-nBu 3-tetrahydrofuranyl 8.19 Me Me SO₂Ph 3-tetrahydrofuranyl 8.20 MeMe CO₂Me 3-tetrahydrofuranyl 8.21 Me Me CO₂Et 3-tetrahydrofuranyl 8.22Me Me CO₂-nPr 3-tetrahydrofuranyl 8.23 Me Me CO₂-nBu 3-tetrahydrofuranyl8.24 Me Me CO₂Ph 3-tetrahydrofuranyl 8.25 Me Me Me 3-tetrahydrofuranyl8.26 Me Me Et 3-tetrahydrofuranyl 8.27 Me Me nPr 3-tetrahydrofuranyl8.28 Me Me nBu 3-tetrahydrofuranyl 8.29 H Et SOMe 3-tetrahydrofuranyl8.30 H Et SOMe 3-tetrahydrofuranyl 8.31 H Et SO₂-nPr 3-tetrahydrofuranyl8.32 H Et SO₂-nBu 3-tetrahydrofuranyl 8.33 H Et SO₂Ph3-tetrahydrofuranyl 8.34 H Et CO₂Me 3-tetrahydrofuranyl 8.35 H Et CO₂Et3-tetrahydrofuranyl 8.36 H Et CO₂-nPr 3-tetrahydrofuranyl 8.37 H EtCO₂-nBu 3-tetrahydrofuranyl 8.38 H Et CO₂Ph 3-tetrahydrofuranyl 8.39 HEt Me 3-tetrahydrofuranyl 8.40 H Et Et 3-tetrahydrofuranyl 8.41 H Et nPr3-tetrahydrofuranyl 8.42 H Et nBu 3-tetrahydrofuranyl 8.43 cPr Me SOMe3-tetrahydrofuranyl 8.44 cPr Me SOMe 3-tetrahydrofuranyl 8.45 cPr MeSO₂-nPr 3-tetrahydrofuranyl 8.46 cPr Me SO₂-nBu 3-tetrahydrofuranyl 8.47cPr Me SO₂Ph 3-tetrahydrofuraflyl 8.48 cPr Me CO₂Me 3-tetrahydrofuranyl8.49 cPr Me CO₂Et 3-tetrahydrofuranyl 8.50 cPr Me CO₂-nPr3-tetrahydrofuranyl 8.51 cPr Me CO₂-nBu 3-tetrahydrofuranyl 8.52 cPr MeCO₂Ph 3-tetrahydrofuranyl 8.53 cPr Me Me 3-tetrahydrofuranyl 8.54 cPr MeEt 3-tetrahydrofuranyl 8.55 cPr Me nPr 3-tetrahydrofuranyl 8.56 cPr MenBu 3-tetrahydrofuranyl 8.57 H Me SOMe 3-tetrahydropyranyl 8.58 H MeSOMe 3-tetrahydropyranyl 8.59 H Me SO₂-nPr 3-tetrahydropyranyl 8.60 H MeSO₂-nBu 3-tetrahydropyranyl 8.61 H Me SO₂Ph 3-tetrahydropyranyl 8.62 HMe CO₂Me 3-tetrahydropyranyl 8.63 H Me CO₂Et 3-tetrahydropyranyl 8.64 HMe CO₂-nPr 3-tetrahydropyranyl 8.65 H Me CO₂-nBu 3-tetrahydropyranyl8.66 H Me CO₂Ph 3-tetrahydropyranyl 8.67 H Me Me 3-tetrahydropyranyl8.68 H Me Et 3-tetrahydropyranyl 8.69 H Me nPr 3-tetrahydropyranyl 8.70H Me nBu 3-tetrahydropyranyl 8.71 Me Me SOMe 3-tetrahydropyranyl 8.72 MeMe SOMe 3-tetrahydropyranyl 8.73 Me Me SO₂-nPr 3-tetrahydropyranyl 8.74Me Me SO₂-nBu 3-tetrahydropyranyl 8.75 Me Me SO₂Ph 3-tetrahydropyranyl8.76 Me Me CO₂Me 3-tetrahydropyranyl 8.77 Me Me CO₂Et3-tetrahydropyranyl 8.78 Me Me CO₂-nPr 3-tetrahydropyranyl 8.79 Me MeCO₂-nBu 3-tetrahydropyranyl 8.80 Me Me CO₂Ph 3-tetrahydropyranyl 8.81 MeMe Me 3-tetrahydropyranyl 8.82 Me Me Et 3-tetrahydropyranyl 8.83 Me MenPr 3-tetrahydropyranyl 8.84 Me Me nBu 3-tetrahydropyranyl 8.85 H EtSOMe 3-tetrahydropyranyl 8.86 H Et SOMe 3-tetrahydropyranyl 8.87 H EtSO₂-nPr 3-tetrahydropyranyl 8.88 H Et SO₂-nBu 3-tetrahydropyranyl 8.89 HEt SO₂Ph 3-tetrahydropyranyl 8.90 H Et CO₂Me 3-tetrahydropyranyl 8.91 HEt CO₂Et 3-tetrahydropyranyl 8.92 H Et CO₂-nPr 3-tetrahydropyranyl 8.93H Et CO₂-nBu 3-tetrahydropyranyl 8.94 H Et CO₂Ph 3-tetrahydropyranyl8.95 H Et Me 3-tetrahydropyranyl 8.96 H Et Et 3-tetrahydropyranyl 8.97 HEt nPr 3-tetrahydropyranyl 8.98 H Et nBu 3-tetrahydropyranyl 8.99 cPr MeSOMe 3-tetrahydropyranyl 8.100 cPr Me SOMe 3-tetrahydropyranyl 8.101 cPrMe SO₂-nPr 3-tetrahydropyranyl 8.102 cPr Me SO₂-nBu 3-tetrahydropyranyl8.103 cPr Me SO₂Ph 3-tetrahydropyranyl 8.104 cPr Me CO₂Me3-tetrahydropyranyl 8.105 cPr Me CO₂Et 3-tetrahydropyranyl 8.106 cPr MeCO₂-nPr 3-tetrahydropyranyl 8.107 cPr Me CO₂-nBu 3-tetrahydropyranyl8.108 cPr Me CO₂Ph 3-tetrahydropyranyl 8.109 cPr Me Me3-tetrahydropyranyl 8.110 cPr Me Et 3-tetrahydropyranyl 8.111 cPr Me nPr3-tetrahydropyranyl 8.112 cPr Me nBu 3-tetrahydropyranyl 8.113 H Me SOMe1,3-dioxan-5-yl 8.114 H Me SOMe 1,3-dioxan-5-yl 8.115 H Me SO₂-nPr1,3-dioxan-5-yl 8.116 H Me SO₂-nBu 1,3-dioxan-5-yl 8.117 H Me SO₂Ph1,3-dioxan-5-yl 8.118 H Me CO₂Me 1,3-dioxan-5-yl 8.119 H Me CO₂Et1,3-dioxan-5-yl 8.120 H Me CO₂-nPr 1,3-dioxan-5-yl 8.121 H Me CO₂-nBu1,3-dioxan-5-yl 8.122 H Me CO₂Ph 1,3-dioxan-5-yl 8.123 H Me Me1,3-dioxan-5-yl 8.124 H Me Et 1,3-dioxan-5-yl 8.125 H Me nPr1,3-dioxan-5-yl 8.126 H Me nBu 1,3-dioxan-5-yl 8.127 Me Me SOMe1,3-dioxan-5-yl 8.128 Me Me SOMe 1,3-dioxan-5-yl 8.129 Me Me SO₂-nPr1,3-dioxan-5-yl 8.130 Me Me SO₂-nBu 1,3-dioxan-5-yl 8.131 Me Me SO₂Ph1,3-dioxan-5-yl 8.132 Me Me CO₂Me 1,3-dioxan-5-yl 8.133 Me Me CO₂Et1,3-dioxan-5-yl 8.134 Me Me CO₂-nPr 1,3-dioxan-5-yl 8.135 Me Me CO₂-nBu1,3-dioxan-5-yl 8.136 Me Me CO₂Ph 1,3-dioxan-5-yl 8.137 Me Me Me1,3-dioxan-5-yl 8.138 Me Me Et 1,3-dioxan-5-yl 8.139 Me Me nPr1,3-dioxan-5-yl 8.140 Me Me nBu 1,3-dioxan-5-yl 8.141 H Et SOMe1,3-dioxan-5-yl 8.142 H Et SOMe 1,3-dioxan-5-yl 8.143 H Et SO₂-nPr1,3-dioxan-5-yl 8.144 H Et SO₂-nBu 1,3-dioxan-5-yl 8.145 H Et SO₂Ph1,3-dioxan-5-yl 8.146 H Et CO₂Me 1,3-dioxan-5-yl 8.147 H Et CO₂Et1,3-dioxan-5-yl 8.148 H Et CO₂-nPr 1,3-dioxan-5-yl 8.149 H Et CO₂-nBu1,3-dioxan-5-yl 8.150 H Et CO₂Ph 1,3-dioxan-5-y1 8.151 H Et Me1,3-dioxan-5-yl 8.152 H Et Et 1,3-dioxan-5-yl 8.153 H Et nPr1,3-dioxan-5-yl 8.154 H Et nBu 1,3-dioxan-5-yl 8.155 cPr Me SOMe1,3-dioxan-5-yl 8.156 cPr Me SOMe 1,3-dioxan-5-yl 8.157 cPr Me SO₂-nPr1,3-dioxan-5-yl 8.158 cPr Me SO₂-nBu 1,3-dioxan-5-yl 8.159 cPr Me SO₂Ph1,3-dioxan-5-yl 8.160 cPr Me CO₂Me 1,3-dioxan-5-yt 8.161 cPr Me CO₂Et1,3-dioxan-5-yl 8.162 cPr Me CO₂-nPr 1,3-dioxan-5-yl 8.163 cPr MeCO₂-nBu 1,3-dioxan-5-yl 8.164 cPr Me CO₂Ph 1,3-dioxan-5-yl 8.165 cPr MeMe 1,3-dioxan-5-yl 8.166 cPr Me Et 1,3-dioxan-5-yl 8.167 cPr Me nPr1,3-dioxan-5-yl 8.168 cPr Me nBu 1,3-dioxan-5-yl 8.169 H Me SOMeγ-butyrolacton-2-yl 8.170 H Me SOMe γ-butyrolacton-2-yl 8.171 H MeSO₂-nPr γ-butyrolacton-2-yl 8.172 H Me SO₂-nBu γ-butyrolacton-2-yl 8.173H Me SO₂Ph γ-butyrolacton-2-yt 8.174 H Me CO₂Me γ-butyrolacton-2-yl8.175 H Me CO₂Et γ-butyrolacton-2-yl 8.176 H Me CO₂-nPrγ-butyrolacton-2-yl 8.177 H Me CO₂-nBu γ-butyrolacton-2-yl 8.178 H MeCO₂Ph γ-bulyrolacton-2-yl 8.179 H Me Me γ-bulyrolacton-2-yl 8.180 H MeET γ-butyrolacton-2-yl 8.181 H Me nPr γ-bulyrolacton-2-yl 8.182 H Me nBuγ-butyrolacton-2-yl 8.183 Me Me SOMe γ-butyrolacton-2-yl 8.184 Me MeSOMe γ-butyrolacton-2-yl 8.185 Me Me SO₂-nPr γ-butyrolacton-2-yl 8.186Me Me SO₂-nBu γ-butyrolacton-2-yl 8.187 Me Me SO₂Ph γ-butyrolacton-2-yl8.188 Me Me CO₂Me γ-butyrolacton-2-yl 8.189 Me Me CO₂Etγ-butyrolacton-2-yl 8.190 Me Me CO₂-nPr γ-butyrolacton-2-yl 8.191 Me MeCO₂-nBu γ-butyrolacton-2-yl 8.192 Me Me CO₂Ph γ-butyrolacton-2-yl 8.193Me Me Me γ-butyrolacton-2-yl 8.194 Me Me Et γ-butyrolacton-2-yl 8.195 MeMe nPr γ-butyrolacton-2-yl 8.196 Me Me nBu γ-butyrolacton-2-yl 8.197 HEt SOMe γ-butyrolacton-2-yl 8.198 H Et SOMe γ-butyrolacton-2-yl 8.199 HEt SO₂-nPr γ-butyrolacton-2-yl 8.200 H Et SO₂-nBu γ-butyrolacton-2-yl8.201 H Et SO₂Ph γ-butyrolacton-2-yl 8.202 H Et CO₂Meγ-butyrolacton-2-yl 8.203 H Et CO₂Et γ-butyrolacton-2-yl 8.204 H EtCO₂-nPr γ-butyrolacton-2-yl 8.205 H Et CO₂-nBu γ-butyrolacton-2-yl 8.206H Et CO₂Ph γ-butyrolacton-2-yl 8.207 H Et Me γ-butyrolacton-2-yl 8.208 HEt Et γ-butyrolacton-2-yl 8.209 H Et nPr γ-butyrolacton-2-yl 8.210 H EtnBu γ-butyrolacton-2-yl 8.211 cPr Me SOMe γ-butyrolacton-2-yl 8.212 cPrMe SOMe γ-butyrolacton-2-yl 8.213 cPr Me SO₂-nPr γ-butyrolacton-2-yl8.214 cPr Me SO₂-nBu γ-butyrolacton-2-yl 8.215 cPr Me SO₂Phγ-butyrolacton-2-yl 8.216 cPr Me CO₂Me γ-butyrolacton-2-yl 8.217 cPr MeCO₂Et γ-butyrolacton-2-yl 8.218 cPr Me CO₂-nPr γ-butyrolacton-2-yl 8.219cPr Me CO₂-nBu γ-butyrolacton-2-yl 8.220 cPr Me CO₂Phγ-butyrolacton-2-yl 8.221 cPr Me Me γ-butyrolacton 2-yl 8.222 cPr Me Etγ-butyrolacton 2-yl 8.223 cPr Me nPr γ-butyrolacton 2-yl 8.224 cPr MenBu γ-butyrolacton 2-yl

B. FORMULATION EXAMPLES

1. Dusts

A dust is obtained by mixing 10 parts by weight of a compound of theformula (I) and 90 parts by weight of talc as inert substance andcomminuting the mixture in a hammer mill.

2. Dispersible Powder

A wettable powder which is readily dispersible in water is obtained bymixing parts by weight of a compound of the formula (I), 64 parts byweight of kaolin-containing quartz as inert substance, 10 parts byweight of potassium lignosulfonate and 1 part by weight of sodiumoleoylmethyltaurate as wetter and dispersant and grinding the mixture ina pinned-disk mill.

3. Dispersion Concentrate

A dispersion concentrate which is readily dispersible in water isobtained by mixing 20 parts by weight of a compound of the formula (I),6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts byweight of paraffinic mineral oil (boiling range, for example, approx.255 to over 277° C.) and grinding the mixture in a friction ball mill toa fineness of below 5 microns.

4. Emulsifiable Concentrate

An emulsifiable concentrate is obtained from 15 parts by weight of acompound of the formula (I), 75 parts by weight of cyclohexanone assolvent and 10 parts by weight of oxethylated nonylphenol as emulsifier.

5. Water-Dispersible Granules

Water-dispersible granules are obtained by mixing

-   75 parts by weight of a compound of the formula (I),-   10 ″ of calcium lignosulfonate,-   5 ″ of sodium lauryl sulfate,-   3 ″ of polyvinyl alcohol and-   7 ″ of kaolin,    grinding the mixture in a pinned-disk mill and granulating the    powder in a fluidized bed by spraying on water as granulating fluid.

Water-dispersible granules are also obtained by homogenizing andprecomminuting

-   25 parts by weight of a compound of the formula (I),-   5 ″ of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,-   2 ″ of sodium oleoylmethyltaurate,-   1 ″ of polyvinyl alcohol,-   17 ″ of calcium carbonate and-   50 ″ of water    in a colloid mill, subsequently grinding the mixture in a bead mill    and atomizing and drying the suspension obtained in a spray tower by    means of a single-substance nozzle.

C. BIOLOGICAL EXAMPLES

1. Herbicidal Action Pre-Emergence

Seeds of mono- and dicotyledonous harmful plants are put into sandy loamin cardboard pots and covered with soil. The compounds according to theinvention, which are formulated in the form of wettable powders oremulsion concentrates, are then applied to the surface of the soil coveras an aqueous suspension or emulsion at an application rate of 600 to800 l/ha (converted) in various dosages. After the treatment, the potsare placed in a greenhouse and kept under good growth conditions for theweeds. Visual scoring of the plant damage or emergence damage is carriedout after the test plants have emerged after a test period of 3 to 4weeks in comparison with untreated controls. After the test plants havestood in the greenhouse under optimum growth conditions for 3 to 4weeks, the effect of the compounds is scored. Here, the compoundsaccording to the invention have excellent activity against a broadspectrum of economically important mono- and dicotyledonous harmfulplants.

Thus, for example, the compound according to the invention of No. 1.1shows, at a dosage of 320 g/ha, at least 90% action against the harmfulplants Galium aparine, Matricaria inodora, Stellaria media, Chenopodiumalbum, Veronica persica and Abutilon theophrasti.

2. Herbicidal Action Post-Emergence

Seeds of mono- and dicotyledonous weeds are put into sandy loam incardboard pots, covered with soil and grown in the greenhouse under goodgrowth conditions. Two to three weeks after sowing, the test plants aretreated in the three-leaf stage. The compounds according to theinvention, which are formulated as wettable powders or as emulsionconcentrates, are sprayed onto the surface of the green plant parts invarious dosages at a water application rate of 600 to 800 l/ha(converted). After the test plants have been left to stand in thegreenhouse for 3 to 4 weeks under optimal growth conditions, the actionof the compounds is scored. The compositions according to the inventionhere show excellent activity against a broad spectrum of economicallyimportant mono- and dicotyledonous harmful plants. Thus, for example,the compound according to the invention of No. 3.1 shows, at a dosage of320 g/ha, an action of at least 80% against the harmful plants Sinapisarvensis, Avena fatua, Amaranthus retroflexus and Setaria viridis.

3. Crop Plant Tolerance

In further experiments in the greenhouse, seeds of barley and mono- anddicotyledonous weeds are put in sandy loam and covered with soil andplaced in the greenhouse until the plants have developed two to threetrue leaves. Treatment with the compounds of the formula (I) accordingto the invention is then carried out as described under item 2. Four tofive weeks after application and after the plants have remained in thegreenhouse, it is found by means of visual scoring that the compoundsaccording to the invention are tolerated extremely well by importantcrop plants, in particular wheat, corn and rice.

Thus, for example, the compound according to the invention of No. 1.1shows, at a dosage of 50 g/ha, at least 95% action against the harmfulplants Echinochloa crusgalli, Sagittaria pygmaea, Cyperus serotinus andScirpus juncoides, while at the same time, the crop plant rice is notdamaged. At a dosage of 320 g/ha, the compound according to theinvention of No. 1.85 shows at least 90% action against the harmfulplants Stellaria media, Veronica persica, Chenopodium album and Abutilontheophrasti, while at the same time no damage is caused to the cropplants rice, wheat and corn.

1. A compound of the formula (I) or a salt thereof

in which the radicals and indices are as defined below: R¹, R²independently of one another are hydrogen, mercapto, nitro, halogen,cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl,—OR⁴, OCOR⁴, OSO₂R⁴, S(O)_(n)R⁴, SO₂OR⁴, SO₂N(R⁴)₂, NR⁴SO₂R⁴, NR⁴COR⁴,C₁-C₆-alkyl-S(O)_(n)R⁴, C₁-C₆-alkyl-OR⁴, C₁-C₆-alkyl-OCOR⁴,C₁-C₆-alkyl-OSO₂R⁴, C₁-C₆-alkyl-SO₂OR⁴, C₁-C₆-alkyl-SO₂N(R⁴)₂ orC₁-C₆-alkyl-NR⁴COR⁴; R³ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl orC₂-C₆-alkynyl; R⁴ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, phenyl or phenyl-C₁-C₆-alkyl, where thesix last-mentioned radicals are substituted by s radicals selected fromthe group consisting of hydroxy, mercapto, amino, cyano, nitro,thiocyanato, OR³, SR³, N(R³)₂, ═NOR³, OCOR³, SCOR³, NR³COR³, CO₂R³,COSR³, CON(R³)₂, C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl andC₁-C₄-alkylsulfonyl; Het is a fully saturated heterocyclic group whosering atoms consist of carbon and oxygen atoms, where the total number ofring atoms is p, the number of oxygen atoms is r, the number of carbonatoms is (p−r) and Het may be substituted by n radicals R⁵; n is 0, 1 or2; p is 5, 6 or 7; r is 1 or 2; s is 0, 1, 2 or 3; X is O or S(O)_(n);R⁵ is hydroxy, mercapto, amino, cyano, nitro, halogen, formyl,C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkoxycarbonyl,C₁-C₆-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy, orC₁-C₆-haloalkoxy or R⁵ together with the carbon atom to which it isattached forms a carbonyl group; Q is a radical of group Q1 or Q2;

R⁶, R⁷ independently of one another are hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl or C₃-C₆-cyclopropyl; R⁸ is hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,phenylcarbonyl, phenylcarbonylmethyl, phenyloxycarbonyl orphenylsulfonyl, where the phenyl ring of the four last-mentionedradicals is substituted by s radicals selected from the group consistingof halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy andC₁-C₆-haloalkoxy.
 2. A compound as claimed in claim 1, in which R¹, R²independently of one another are hydrogen, nitro, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl, —OR⁴, S(O)_(n)R⁴, SO₂OR⁴,SO₂N(R⁴)₂, NR⁴SO₂R⁴ or C₁-C₆-alkyl-S(O)_(n)R⁴; R⁴ is hydrogen,C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, phenyl orphenyl-C₁-C₄-alkyl, where the six last-mentioned radicals aresubstituted by s radicals selected from the group consisting of cyano,nitro, R³, OR³, SR³ and N(R³)₂.
 3. A compound as claimed in claim 1, inwhich R³ is hydrogen; R⁵ is cyano, nitro, halogen, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₆-alkoxy, orC₁-C₆-haloalkoxy, or R⁵ together with the carbon atom to which it isattached forms a carbonyl group.
 4. A compound as claimed in claim 1, inwhich R⁶, R⁷ independently of one another are hydrogen or C₁-C₄-alkyl;R⁸ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylcarbonyl,C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylsulfonyl,C₁-C₄-haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl,phenyloxycarbonyl or phenylsulfonyl, where the phenyl ring of the fourlast-mentioned radicals is substituted by s radicals selected from thegroup consisting of halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.
 5. A compound as claimed in claim 1,in which R¹ is chlorine, bromine, iodine, nitro, methyl, thiomethyl,thioethyl, methylsulfonyl, ethylsulfonyl or methoxy; R² is bromine,chlorine, methylsulfonyl or ethylsulfonyl; R² is located in the4-position of the phenyl ring; R⁸ is hydrogen, Het is3-tetrahydrofuranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl,1,3-dioxan-5-yl or γ-butyrolacton-2-yl.
 6. A herbicidal compositionwhich comprises a herbicidally effective amount of at least one compoundof the formula (I) as claimed in claim
 1. 7. A herbicidal composition asclaimed in claim 6 in a mixture with formulation auxiliaries.
 8. Amethod for controlling unwanted plants, which comprises applying aneffective amount of at least one compound of the formula (I) as claimedin claim 1 to the plants or the site where the unwanted plants arelocated.
 9. A method of using the compound of the formula (I) as claimedin claim 1 for controlling unwanted plants, wherein said compound of theformula (I) is applied to the unwanted plants or to the locus of theunwanted plants.
 10. The method as claimed in claim 9, wherein the locusof the unwanted plants also contains useful plants.
 11. The method asclaimed in claim 10, wherein the useful plants are transgenic usefulplants.
 12. A method for controlling unwanted plants, which comprisesapplying an effective amount of the herbicidal composition of claim 6 tothe plants or the site where the unwanted plants are located.
 13. Amethod of using the herbicidal composition of claim 6 for controllingunwanted plants, wherein said composition is applied to the unwantedplants or to the locus of the unwanted plants.
 14. A method ofcontrolling unwanted plants in a locus that contains both unwantedplants and useful plants, said method comprising the step of applyingthe herbicidal composition of claim 6 to said locus.